反应 #1948551
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openreactiondata ↗doi:10.6084/m9.figshare.5104873.v1; patent:US07375248B2
反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: t-Butylbromoacetate (1.12 g, 0.85 mL, 5.76 mmol) was added drop wise over 5 min to a stirred suspension of {4-[(3-methylbutyl)oxy]phenyl}amine (intermediate 5, 0.85 g, 4.8 mmol) and potassium carbonate (0.66 g, 4.8 mmol) in dimethylformamide (23.4 mL) at room temperature under a nitrogen atmosphere. After stirring for 14 h the volatiles were evaporated and the residue partitioned between dichloromethane (50 mL) and water (50 mL). The phases were separated and the aqueous phase washed with dichloromethane (2×50 mL). The organic phases were combined, dried (magnesium sulfate) then the solvent evaporated. The residue was chromatographed on silica gel (10% diethyl ether:cyclohexane) to give the title compound (inseparable 10:1 mixture of mono- to di-substitution) as a colourless oil (1.38 g). Mono-product: LC/MS: 3.77 min; z/e 294, calcd (M+1) 294. 1H NMR (400 MHz; CDCl3): 0.90 (6H), 1.45 (9H), 1.65 (2H), 1.85 (1H), 3.75 (2H), 3.90 (2H), 6.55 (2H), 6.80 (2H). were evaporated the residue partitioned between dichloromethane (50 mL) and water (50 mL) The phases were separated the aqueous phase washed with dichloromethane (2×50 mL) dried (magnesium sulfate) the solvent evaporated The residue was chromatographed on silica gel (10% diethyl ether:cyclohexane)
来源 ID: ord-befff2d431fc4120936bc1a735a7e14f