Sulfoxonium, trimethyl-, iodide (1:1) → 1-[4'-(3-Methyl-4-oxiranyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

HRID 1183315ノート

反応式

HRID 1183315 の反応式
[CH2:1]([Li])CCC.[I-].C[S+](C)(C)=O.[CH2:12]([O:14][C:15]([C:17]1([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]4[O:36][N:35]=[C:34]([CH3:37])[C:33]=4[CH:38]=[O:39])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH2:19][CH2:18]1)=[O:16])[CH3:13]>CS(C)=O>[CH2:12]([O:14][C:15]([C:17]1([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]4[O:36][N:35]=[C:34]([CH3:37])[C:33]=4[CH:38]4[CH2:1][O:39]4)=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)[CH2:19][CH2:18]1)=[O:16])[CH3:13]

参加物

5

反応物 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 866524021-[4'-(4-Formyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl esterHCID 178418339Butyllithium

生成物 1

HCID 866524031-[4'-(3-Methyl-4-oxiranyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

n-Butyllithium (1.6M in hexanes, 2.30 mL, 3.69 mmol) was placed in a flask along with DMSO (8 mL) and the solution was placed under N2 atmosphere. Trimethyl sulfoxonium iodide (0.963 g, 4.29 mmol) was added and stirred for 5 minutes. 1-[4′-(4-Formyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.46 g, 1.23 mmol) in DMSO (8 mL) was then added and the reaction was stirred. After 40 minutes the reaction was quenched with ice then submitted to standard aqueous workup and purified on silica gel (0-40% EtOAc in hexanes) to afford the title compound.

後処理

  1. stirringthe reaction was stirred
  2. customAfter 40 minutes the reaction was quenched with ice
  3. custompurified on silica gel (0-40% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-4cfdfcc0376c4e118aca8cce8b9ea64a
出典データセット
uspto-grants-2014_03
特許番号
US08664220B2

反応ノート

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