Triethylamine → 1-Methanesulfonyloxymethyl-cyclopropanecarboxylic acid ethyl ester

HRID 1428368

반응식

HRID 1428368 반응식
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[OH:13][CH2:14][C:15]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:17][CH2:16]1>ClCCl.O>[CH3:8][S:9]([O:13][CH2:14][C:15]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:17][CH2:16]1)(=[O:11])=[O:10]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 12450336Ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylate

생성물 1

HCID 574666101-Methanesulfonyloxymethyl-cyclopropanecarboxylic acid ethyl ester수율 94%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
23 °C

실험 절차

Triethylamine (5.57 mL, 40.00 mmol) and methanesulfonyl chloride (2.85 mL, 36.60 mmol) were sequentially added to a stirred solution of ethyl 1-(hydroxymethyl)cyclopropanecarboxylate (4.80 g, 33.30 mmol) in dichloromethane (83 mL) at 23° C. The resulting bright yellow solution was stirred at 23° C. for 20 h. The reaction mixture was diluted with water and extracted with dichloromethane. The combined organic layers were dried (MgSO4), filtered, and concentrated to dryness to give the desired product as a brown oil (6.92 g, 94%): 1H NMR (300 MHz, CDCl3) δ 4.33 (s, 2H), 4.16 (q, J=7 Hz, 2H), 3.08 (s, 3H), 1.43 (dd, J=7, 4 Hz, 2H), 1.26 (t, J=7 Hz, 3H), 1.04 (dd, J=7, 4 Hz, 2H).

후처리

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-95d3ba03b4304c349d5c61f0598d0543
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937083B2

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