4-甲基-4-苯基-2-戊酮

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of NaOH (47.2 g, 1.18 mole) in ice/H2O (270 g) maintained at 4°-5° C. was added Br2 (68.7 g, 0.43 mole) followed by 4-methyl-4-phenyl-2-pentanone (23.7 g, 0.135 mole). The reaction was stirred for 18 hours at room temperature. The crude reaction mixture was extracted with CCl4 (discarded), acidified to pH 1-2 with concentrated HCl solution and extracted with ethyl acetate. The combined organics were washed with saturated NaCl solution, dried over Na2SO4 and evaporated in vacuo to obtain 22.5 g of the title B compound as an off-white solid. This was used in the next step without further purification. MS: (M+NH4)+ @ 196. The crude reaction mixture was extracted with CCl4 (discarded) extracted with ethyl acetate The combined organics were washed with saturated NaCl solution dried over Na2SO4 evaporated in vacuo to obtain 22.5 g of the title B compound as an off-white solid This was used in the next step without further purification

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a slurry of AlCl3 (40.0 g, 0.3 mole) in benzene (90 mL) maintained at 10° C. under argon was added dropwise mesityl oxide (0.2 mole, 19.63 g). Upon completion of the addition the reaction was stirred at room temperature for 1.5 hours. The reaction mixture was poured onto ice/10% HCl (350 g). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organics were washed with distilled H2O, saturated NaHCO3 solution, saturated NaCl solution and dried over Na2SO4. The solvent was recovered under vacuum and the crude product (31.6 g) was vacuum distilled (b.p.=107° C. @ 3.0 mmHg) to obtain 24.5 g (69%) of the title A compound as a colorless oil. MS: (M+H)+ @ 177. Upon completion of the addition the reaction The reaction mixture was poured onto ice/10% HCl (350 g) The organic layer was separated the aqueous layer was extracted with ethyl acetate (100 mL) The combined organics were washed with distilled H2O, saturated NaHCO3 solution, saturated NaCl solution dried over Na2SO4 The solvent was recovered under vacuum distilled (b.p.=107° C. @ 3.0 mmHg)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a slurry of AlCl3 (40.0 g, 0.3 mole) in benzene (90 mL) maintained at 10° C. under argon was added dropwise mesityl oxide (0.2 mole, 19.63 g). Upon completion of the addition the reaction was stirred at room temperature for 1.5 hours. The reaction mixture was poured onto ice/10% HCl (350 g). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organics were washed with distilled H2O, saturated NaHCO3 solution, saturated NaCl solution and dried over Na2SO4. The solvent was recovered under vacuum and the crude product (31.6 g) was vacuum distilled (b.p.=107° C. @ 3.0 mmHg) to obtain 24.5 g (69%) of the title A compound as a colorless oil. MS: (M+H)+ @ 177. Upon completion of the addition the reaction The reaction mixture was poured onto ice/10% HCl (350 g) The organic layer was separated the aqueous layer was extracted with ethyl acetate (100 mL) The combined organics were washed with distilled H2O, saturated NaHCO3 solution, saturated NaCl solution dried over Na2SO4 The solvent was recovered under vacuum distilled (b.p.=107° C. @ 3.0 mmHg)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: CMP can be prepared by reacting benzene with mesityl oxide to form 4-methyl-4-phenyl-2-pentanone which is then subjected to appropriate hydrogenation. CMP can be prepared

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a slurry of aluminum chloride (40.0 g, 0.3 mole) in benzene (90 ml) maintained at 10° C. under argon was added dropwise mesityl oxide (19.63 g, 0.2 mole). Upon completion of the addition the reaction was stirred at room temperature for 1.5 hours. The reaction mixture was poured onto ice/10% HCl (350 g). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 ml). The combined organics were washed with distilled water, saturated sodium hydrogen carbonate solution, saturated sodium chloride solution and dried over sodium sulfate. The solvent was evaporated under vacuum and the crude product (31.6 g) was vacuum distilled (b.p.=107° C. at 3.0 mmHg) to obtain 24.5 g of the title A compound as a colorless oil. 1H NMR (CDCl3) δ 7.38-7.19 (m, 5H), 2.74 (s, 2H), 1.80 (s, 3H), 1.43 (s, 6H). 13C NMR (CDCl 3) δ 207.94, 148.16, 128.26, 125.95, 125.46, 56.96, 37.29, 31.76, 28.88. Upon completion of the addition the reaction The reaction mixture was poured onto ice/10% HCl (350 g) The organic layer was separated the aqueous layer was extracted with ethyl acetate (100 ml) The combined organics were washed with distilled water, saturated sodium hydrogen carbonate solution, saturated sodium chloride solution dried over sodium sulfate The solvent was evaporated under vacuum distilled (b.p.=107° C. at 3.0 mmHg)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Prepared according to the procedure described in Example 24, Step 1, using 5-(4-bromo-phenyl)-3-methyl-isoxazol-4-ylamine and 4-methyl-4-phenyl-pentan-2-one. Prepared

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Prepared according to the procedure described in Example 8, Step 1, using 5-(4-bromo-phenyl)-3-methyl-isoxazol-4-ylamine and 4-methyl-4-phenyl-pentan-2-one. Prepared

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of NaOH (47.2 g, 1.18 mole) in ice/H2O (270 g) maintained at 4°-5° C. was added Br2 (68.7 g, 0.43 mole) followed by 4-methyl-4-phenyl-2-pentanone (23.7 g, 0.135 mole). The reaction was stirred for 18 hours at room temperature. The crude reaction mixture was extracted with CCl4 (discarded), acidified to pH 1-2 with concentrated HCl solution and extracted with ethyl acetate. The combined organics were washed with saturated NaCl solution, dried over Na2SO4 and evaporated in vacuo to obtain 22.5 g of the title B compound as an off-white solid. This was used in the next step without further purification. MS: (M+NH4)+ @ 196. The crude reaction mixture was extracted with CCl4 (discarded) extracted with ethyl acetate The combined organics were washed with saturated NaCl solution dried over Na2SO4 evaporated in vacuo to obtain 22.5 g of the title B compound as an off-white solid This was used in the next step without further purification

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a slurry of AlCl3 (40.0 g, 0.3 mole) in benzene (90 mL) maintained at 10° C. under argon was added dropwise mesityl oxide (0.2 mole, 19.63 g). Upon completion of the addition the reaction was stirred at room temperature for 1.5 hours. The reaction mixture was poured onto ice/10% HCl (350 g). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organics were washed with distilled H2O, saturated NaHCO3 solution, saturated NaCl solution and dried over Na2SO4. The solvent was recovered under vacuum and the crude product (31.6 g) was vacuum distilled (b.p.=107° C. @ 3.0 mmHg) to obtain 24.5 g (69%) of the title A compound as a colorless oil. MS: (M+H)+ @ 177. Upon completion of the addition the reaction The reaction mixture was poured onto ice/10% HCl (350 g) The organic layer was separated the aqueous layer was extracted with ethyl acetate (100 mL) The combined organics were washed with distilled H2O, saturated NaHCO3 solution, saturated NaCl solution dried over Na2SO4 The solvent was recovered under vacuum distilled (b.p.=107° C. @ 3.0 mmHg)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Methyl magnesium bromide (3M solution in diethyl ether, 22.2 mL, 66.6 mmol) was added slowly to a solution of 4-methyl-4-phenyl-pentan-2-one (Compound 40, 7.8 g, 44.3 mmol) in 50 mL of tetrahydrofuran (THF) at 0° C. After stirring and warming to room temperature for 2 h, the mixture was quenched with water at 0° C., extracted with ethyl acetate (3×10 mL), washed with brine (1×10 mL), dried (MgSO4) and concentrated at reduced pressure to give a light yellow oil. The crude oil was then added slowly to 80% concentrated sulfuric acid at 0° C. and the resulting brown mixture was stirred at 0° C. for 1 h. The mixture was then slowly diluted with ice water, extracted with pentane (3×15 mL) and washed with brine (1×15 mL). After the extract was dried (MgSO4) and concentrated at reduced pressure, high-vacuum distillation of the residue afforded indan the title compound (3.3 g, 43% yield) as a colorless oil: the mixture was quenched with water at 0° C. extracted with ethyl acetate (3×10 mL) washed with brine (1×10 mL) dried (MgSO4) concentrated at reduced pressure to give a light yellow oil the resulting brown mixture was stirred at 0° C. for 1 h extracted with pentane (3×15 mL) washed with brine (1×15 mL) After the extract was dried (MgSO4) concentrated at reduced pressure, high-vacuum distillation of the residue