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

HRID 533345노트

반응식

HRID 533345 반응식
[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]

참가 물질

5

반응물 2

HCID 83542beta-Chloropivalic acidHCID 4378561Sodium methanethiolate

생성물 1

HCID 141470242,2-Dimethyl-3-(methylsulfanyl)propanoic acid

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
23 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2b9330a038404f11a46ec36a52b00f67
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853246B2

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