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

HRID 471425

反応式

HRID 471425 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 962Water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-18e8175939e444b8b598cd845679290a
出典データセット
uspto-grants-2014_01
特許番号
US08633182B2

関連ノート

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