beta-Chloropivalic acid → 2,2-Dimethyl-3-(methylsulfanyl)propanoic acid
Reaction equation
[CH3:1][S-:2].[Na+].Cl[CH2:5][C:6]([CH3:11])([CH3:10])[C:7]([OH:9])=[O:8]>CN(C)C=O.C(=O)(O)[O-].[Na+]>[CH3:10][C:6]([CH3:11])([CH2:5][S:2][CH3:1])[C:7]([OH:9])=[O:8]Participants
Conditions
- Temperature
- 23 °C
Procedure
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 (Na2SO4), gravity-filtered, and concentrated by rotary evaporation to afford the title compound as a colorless oil (1.2 g, 99%): 1H NMR (300 MHz, CDCl3) δ 2.76 (s, 2H), 2.16 (s, 3H), 1.30 (s, 6H).
Workup
- washwashed with diethyl ether (3×75 mL)
- extractionextracted with diethyl ether (3×75 mL)
- dry with materialThe combined organic layers were dried (Na2SO4)
- filtrationgravity-filtered
- concentrationconcentrated by rotary evaporation
Sources & evidence
- ORD record
- ord-86a71581745d48aabc3e8428f0f18e3d
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08912338B2
Reaction notes
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