beta-Chloropivalic acid → 2,2-Dimethyl-3-(methylsulfanyl)propanoic acid

Temperature

23 °C

Example 75 can be prepared as demonstrated in the literature (reference Musker, W. K.; et al. J. Org. Chem. 1996, 51, 1026-1029). Sodium methanethiolate (1.0 g, 14 mmol, 2.0 equiv) was added to a stirred solution of 3-chloro-2,2-dimethylpropanoic acid (1.0 g, 7.2 mmol, 1.0 equiv) in N,N-dimethylformamide (3.7 mL) at 0° C. The resulting brown suspension was allowed to warm to 23° C. and stirred for 24 h. The reaction mixture was diluted with a saturated solution of sodium bicarbonate (300 mL) and washed with diethyl ether (3×75 mL). The aqueous layer was acidified to pH≈1 with concentrated hydrochloric acid and extracted with diethyl ether (3×75 mL). The combined organic layers were dried (sodium sulfate), gravity filtered, and concentrated to afford a colorless oil (1.2 g, 99% crude yield). 1H NMR (300 MHz, CDCl3) δ 2.76 (s, 2H), 2.16 (s, 3H), 1.30 (s, 6H).

1. customExample 75 can be prepared
2. washwashed with diethyl ether (3×75 mL)
3. extractionextracted with diethyl ether (3×75 mL)
4. dry with materialThe combined organic layers were dried (sodium sulfate), gravity
5. filtrationfiltered
6. concentrationconcentrated
7. customto afford a colorless oil (1.2 g, 99% crude yield)

ORD record

ord-5d3e7abb9f974e70a14af19ea4f992c5

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09357780B2