(3R)-4-chlorobutane-1,3-diol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Thus obtained (R)-4-chloro-1,3-butanediol (35.8 g, 0.287 mol) was dissolved in 2,6-lutidine (180 mL). After adding p-toluenesulfonyl chloride (54.8 g, 287 mol) under ice cooling, temperature of the mixture was raised to room temperature and the mixture was stirred for 15 hours. After the reaction, 2,6-lutidine was removed in vacuo. To the residue were added ethyl acetate (150 mL) and water (75 mL) and the mixture was separated by a separating funnel. The organic layer was washed with 2N hydrochloric acid (100 mL) and saturated brine (70 mL), and the solvent was removed in vacuo to give (R)-4-chloro-3-hydroxy-1-p-toluenesulfonyloxybutane (56.7 g, yield: 70.8%). was removed in vacuo To the residue were added ethyl acetate (150 mL) and water (75 mL) the mixture was separated by a separating funnel The organic layer was washed with 2N hydrochloric acid (100 mL) and saturated brine (70 mL) the solvent was removed in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Thus obtained (R)-4-chloro-1,3-butanediol (35.8 g, 0.287 mol) was dissolved in 2,6-lutidine (180 mL). After adding p-toluenesulfonyl chloride (54.8 g, 287 mol) under ice cooling, temperature of the mixture was raised to room temperature and the mixture was stirred for 15 hours. After the reaction, 2,6-lutidine was removed in vacuo. To the residue were added ethyl acetate (150 mL) and water (75 mL) and the mixture was separated by a separating funnel. The organic layer was washed with 2N hydrochloric acid (100 mL) and saturated brine (70 mL), and the solvent was removed in vacuo to give (R)-4-chloro-3-hydroxy-1-p-toluenesulfonyloxybutane (56.7 g, yield: 70.8%). was removed in vacuo To the residue were added ethyl acetate (150 mL) and water (75 mL) the mixture was separated by a separating funnel The organic layer was washed with 2N hydrochloric acid (100 mL) and saturated brine (70 mL) the solvent was removed in vacuo

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 5 g (40 mmole) of (3R)-4-chloro-1,3-butanediol in 30 ml of methylene chloride, said (3R)-4-chloro-1,3-butanediol being obtainable in a similar manner as in Example 1 starting from methyl (3R)-4-chloro-3-hydroxybutyrate, was cooled to -20° C. on a dry ice-acetone bath, and 8.13 g (80 mmole) of triethylamine was added dropwise thereto over 30 minutes. A solution of 7.66 g (40.2 mmole) of p-toluenesulfonyl chloride in 100 ml of methylene chloride was added dropwise thereto over 50 minutes. After returning to room temperature, the mixture was stirred for 20 hours. The reaction mixture was poured into 200 ml of ice-water for liquid separation. The organic layer was washed successively with 100 ml of 1N hydrochloric acid, 100 ml ×2 of a saturated sodium hydrogencarbonate aqueous solution and 100 ml of a saturated sodium chloride aqueous solution and then freed of the solvent by distillation to obtain 7.8 g of a concentrate. The concentrate was purified by silica gel column chromatography (hexane/ethyl acetate=2:1 by volume) to obtain 6.1 g (yield: 54%) of the titled compound. 1H-NMR (CDCl3) δ ppm: 1.78-2.00 (m, 2H), 2.46 (s, 3H), 3.45-3.65 (dd, 2H), 3.95 (m, 1H), 4.20 (m, 2H), 7.40 (d, 2H), 7.80 (d, 2H) over 50 minutes After returning to room temperature The organic layer was washed successively with 100 ml of 1N hydrochloric acid, 100 ml ×2 of a saturated sodium hydrogencarbonate aqueous solution and 100 ml of a saturated sodium chloride aqueous solution freed of the solvent by distillation to obtain 7.8 g of a concentrate The concentrate was purified by silica gel column chromatography (hexane/ethyl acetate=2:1 by volume)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Thus obtained (R)-4-chloro-1,3-butanediol (35.8 g, 0.287 mol) was dissolved in 2,6-lutidine (180 mL). After adding p-toluenesulfonyl chloride (54.8 g, 287 mol) under ice cooling, temperature of the mixture was raised to room temperature and the mixture was stirred for 15 hours. After the reaction, 2,6-lutidine was removed in vacuo. To the residue were added ethyl acetate (150 mL) and water (75 mL) and the mixture was separated by a separating funnel. The organic layer was washed with 2N hydrochloric acid (100 mL) and saturated brine (70 mL), and the solvent was removed in vacuo to give (R)-4-chloro-3-hydroxy-1-p-toluenesulfonyloxybutane (56.7 g, yield: 70.8%). was removed in vacuo To the residue were added ethyl acetate (150 mL) and water (75 mL) the mixture was separated by a separating funnel The organic layer was washed with 2N hydrochloric acid (100 mL) and saturated brine (70 mL) the solvent was removed in vacuo