4-Toluenesulfonyl chloride → HCID 16050326, compound

Temperature

-20 °C

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)

1. waitover 50 minutes
2. customAfter returning to room temperature
3. washThe 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
4. distillationfreed of the solvent by distillation
5. customto obtain 7.8 g of a concentrate
6. customThe concentrate was purified by silica gel column chromatography (hexane/ethyl acetate=2:1 by volume)

ORD record

ord-5f11738fe0c940c4b0ddecf34c7b37e9

Source dataset

uspto-grants-1992_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05144042