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

HRID 1183315노트

반응식

HRID 1183315 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4cfdfcc0376c4e118aca8cce8b9ea64a
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664220B2

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