Sodium hydride → rac-ethyl (1R,2R)-2-(4-methoxyphenyl)cyclopropane-1-carboxylate

HRID 471425

반응식

HRID 471425 반응식
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH2:9]([O:11][C:12](=[O:23])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH3:10]>CS(C)=O.O>[CH2:9]([O:11][C:12]([C@@H:13]1[CH2:2][C@H:14]1[C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)=[O:23])[CH3:10]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 74728Ethyl 4-methoxycinnamate

생성물 1

HCID 818082rac-ethyl (1R,2R)-2-(4-methoxyphenyl)cyclopropane-1-carboxylate수율 26.8%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 962Water용매

실험 절차

Trimethylsulfoxonium iodide (14.15 g, 63 mmol) is suspended in dry DMSO (126 mL) and Sodium hydride (60% in mineral oil, 2.52 g, 63 mmol) is added. The mixture is stirred for 40 minutes and then a solution of 4-methoxycinnamic acid ethyl ester (5 g, 24.2 mmol) in dry DMSO (64 mL) is added and the mixture stirred for 3 hours at room temperature. The mixture is diluted with water and extracted with ethyl acetate, the organic phase is dried by passing through a phase seperator and the solvent is removed under vacuum. The residue is purified by flash chromatography (10% ethyl acetate in cyclohexane) to give the title compound (yield 1.43 g).

후처리

  1. stirringthe mixture stirred for 3 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. customthe organic phase is dried
  4. customthe solvent is removed under vacuum
  5. customThe residue is purified by flash chromatography (10% ethyl acetate in cyclohexane)

출처 및 근거

ORD 기록
ord-18e8175939e444b8b598cd845679290a
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633182B2

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