(E)-1,2-二氯丙-1-烯

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

实验步骤: Dry Mg (0.58 g) under dry N2 in a flask is covered with THF (5 ml) and a crystal of I2 added. 5 ml of a solution of 4-bromobenzaldehyde ethylene acetal (5.0 g) in THF (25 ml) is added and kept until it becomes warm, when it is cooled to 15°, and the remainder of the acetal added over 15 min. then stirred for an additional 1 hour. A mixture of ground lithium chloride (0.35 g) and copper (I) chloride (0.70 g) dissolved in THF is prepared, treated with 1,2-dichloropropene (CH2Cl.CCl=CH2) (4.5 g) and cooled to -20°. The above Grignard solution (under moisture excluding conditions) is then added to this solution during 5 min, and allowed to warm to 20° with stirring for 16 hours. Saturated aqueous ammonium chloride is added and the organic layer evaporated under reduced pressure to a small residue, which is dissolved in THF (100 ml), cooled to -10°, treated with 3N HCl (50 ml), then stirred at 20° for 1 hour. The product is partitioned between ether and water, and the ether layer washed with NaHCO3, H2O NaCl, dried (MgSO4) and the residue chromatographed on florisil. The fraction eluted by 15% ether in petrol is collected and purified by preparative HPLC. Yield 0.55 g (13%) nD20 1.5571. becomes warm when it is cooled to 15° is prepared cooled to -20° The above Grignard solution (under moisture excluding conditions) is then added to this solution during 5 min to warm to 20° with stirring for 16 hours the organic layer evaporated under reduced pressure to a small residue, which is dissolved in THF (100 ml) cooled to -10° treated with 3N HCl (50 ml) stirred at 20° for 1 hour The product is partitioned between ether and water the ether layer washed with NaHCO3, H2O NaCl dried (MgSO4) the residue chromatographed on florisil The fraction eluted by 15% ether in petrol is collected purified by preparative HPLC

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

实验步骤: Dry Mg (0.58 g) under dry N2 in a flask is covered with THF (5 ml) and a crystal of I2 added. 5 ml of a solution of 4-bromobenzaldehyde ethylene acetal (5.0 g) in THF (25 ml) is added and kept until it becomes warm, when it is cooled to 15°, and the remainder of the acetal added over 15 min. then stirred for an additional 1 hour. A mixture of ground lithium chloride (0.35 g) and copper (I) chloride (0.70 g) dissolved in THF is prepared, treated with 1,2-dichloropropene (CH2Cl.CCl=CH2) (4.5 g) and cooled to -20°. The above Grignard solution (under moisture excluding conditions) is then added to this solution during 5 min, and allowed to warm to 20° with stirring for 16 hours. Saturated aqueous ammonium chloride is added and the organic layer evaporated under reduced pressure to a small residue, which is dissolved in THF (100 ml), cooled to -10°, treated with 3N HCl (50 ml), then stirred at 20° for 1 hour. The product is partitioned between ether and water, and the ether layer washed with NaHCO3, H2O NaCl, dried (MgSO4) and the residue chromatographed on florisil. The fraction eluted by 15% ether in petrol is collected and purified by preparative HPLC. Yield 0.55 g (13%) nD20 1.5571. becomes warm when it is cooled to 15° is prepared cooled to -20° The above Grignard solution (under moisture excluding conditions) is then added to this solution during 5 min to warm to 20° with stirring for 16 hours the organic layer evaporated under reduced pressure to a small residue, which is dissolved in THF (100 ml) cooled to -10° treated with 3N HCl (50 ml) stirred at 20° for 1 hour The product is partitioned between ether and water the ether layer washed with NaHCO3, H2O NaCl dried (MgSO4) the residue chromatographed on florisil The fraction eluted by 15% ether in petrol is collected purified by preparative HPLC

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

实验步骤: Dry Mg (0.58 g) under dry N2 in a flask is covered with THF (5 ml) and a crystal of I2 added. 5 ml of a solution of 4-bromobenzaldehyde ethylene acetal (5.0 g) in THF (25 ml) is added and kept until it becomes warm, when it is cooled to 15°, and the remainder of the acetal added over 15 min, then stirred for an additional 1 hour. A mixture of ground lithium chloride (0.35 g) and copper (I) chloride (0.70 g) dissolved in THF is prepared, treated with 1,2-dichloropropene (CH2Cl.CCl=CH2) (4.5 g) and cooled to -20°. The above Grignard solution (under moisture excluding conditions) is then added to this solution during 5 min, and allowed to warm to 20° with stirring for 16 hours. Saturated aqueous ammonium chloride is added and the organic layer evaporated under reduced pressure to a small residue, which is dissolved in THF (100 ml), cooled to -100°, treated with 3N HCl (50 ml), then stirred at 20° for 1 hour. The product is partitioned between ether and water, and the ether layer washed with NaHCO3, H2O NaCl, dried (MgSO4) and the residue chromatographed on florisil. The fraction eluted by 15% ether in petrol is collected and purified by preparative HPLC. Yield 0.50 g (13%) nD20 1.5571. becomes warm when it is cooled to 15° is prepared cooled to -20° The above Grignard solution (under moisture excluding conditions) is then added to this solution during 5 min to warm to 20° with stirring for 16 hours the organic layer evaporated under reduced pressure to a small residue, which is dissolved in THF (100 ml) cooled to -100° treated with 3N HCl (50 ml) stirred at 20° for 1 hour The product is partitioned between ether and water the ether layer washed with NaHCO3, H2O NaCl dried (MgSO4) the residue chromatographed on florisil The fraction eluted by 15% ether in petrol is collected purified by preparative HPLC

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

实验步骤: Dry Mg (0.58 g) under dry N2 in a flask is covered with THF (5 ml) and a crystal of I2 added. 5 ml of a solution of 4-bromobenzaldehyde ethylene acetal (5.0 g) in THF (25 ml) is added and kept until it becomes warm, when it is cooled to 15°, and the remainder of the acetal added over 15 min. then stirred for an additional 1 hour. A mixture of ground lithium chloride (0.35 g) and copper (I) chloride (0.70 g) dissolved in THF is prepared, treated with 1,2-dichloropropene (CH2Cl.CCl=CH2) (4.5 g) and cooled to -20°. The above Grignard solution (under moisture excluding conditions) is then added to this solution during 5 min, and allowed to warm to 20° with stirring for 16 hours. Saturated aqueous ammonium chloride is added and the organic layer evaporated under reduced pressure to a small residue, which is dissolved in THF (100 ml), cooled to -10°, treated with 3N HCl (50 ml), then stirred at 20° for 1 hour. The product is partitioned between ether and water, and the ether layer washed with NaHCO3, H2O NaCl, dried (MgSO4) and the residue chromatographed on florisil. The fraction eluted by 15% ether in petrol is collected and purified by preparative HPLC. Yield 0.55 g (13%) nD20 1.5571. becomes warm when it is cooled to 15° is prepared cooled to -20° The above Grignard solution (under moisture excluding conditions) is then added to this solution during 5 min to warm to 20° with stirring for 16 hours the organic layer evaporated under reduced pressure to a small residue, which is dissolved in THF (100 ml) cooled to -10° treated with 3N HCl (50 ml) stirred at 20° for 1 hour The product is partitioned between ether and water the ether layer washed with NaHCO3, H2O NaCl dried (MgSO4) the residue chromatographed on florisil The fraction eluted by 15% ether in petrol is collected purified by preparative HPLC