Pyridine → (S)-3-(methylsulfonyloxy)butyl benzoate

Temperature

0 °C

To a mixture of (S)-butane-1,3-diol (0.2450 g, 2.718 mmol), pyridine (1.50 mL, 18.5 mmol), and methylene chloride (10.0 mL, 156 mmol) at −15° C. was dropwise added benzoyl chloride (0.32 mL, 2.8 mmol). After 3.5 hours, methanesulfonyl chloride (0.300 mL, 3.88 mmol) was added to the reaction mixture, and the temperature was maintained at 0° C. After 1.5 hours, the reaction was warmed to room temperature. After 2 additional hours, triethylamine (1.0 mL, 7.2 mmol) was added. After one additional hour, the reaction mixture was poured into 50 mL dichloromethane and washed once with 50 mL water. The aqueous layer was extracted with an additional 50 mL of dichloromethane. The combined organic portions were dried over MgSO4, filtered, and evaporated in vacuo. The crude material was purified via flash chromatography on silica gel (40 g silica, solvent gradient: 0-100% ethyl acetate in heptanes) to yield 0.3603 g (49%) of (S)-3-(methylsulfonyloxy)butyl benzoate. LCMS (ESI): M+H=273.2; 1H NMR (400 MHz, DMSO-d6) δ 7.99 (d, J=7.6 Hz, 2H), 7.66 (t, J=7.4 Hz, 1H), 7.53 (t, J=7.7 Hz, 2H), 4.94 (h, J=6.3 Hz, 1H), 4.45-4.26 (m, 2H), 3.17 (s, 3H), 2.09 (q, J=6.2 Hz, 2H), 1.42 (d, J=6.3 Hz, 3H).

1. waitAfter 1.5 hours
2. temperaturethe reaction was warmed to room temperature
3. washwashed once with 50 mL water
4. extractionThe aqueous layer was extracted with an additional 50 mL of dichloromethane
5. dry with materialThe combined organic portions were dried over MgSO4
6. filtrationfiltered
7. customevaporated in vacuo
8. customThe crude material was purified via flash chromatography on silica gel (40 g silica, solvent gradient: 0-100% ethyl acetate in heptanes)

ORD record

ord-e26a4c96fa194ec4aca02fdeb8ab0006

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08623889B2