Water → Ethyl 1-(2,6-dimethoxyphenyl)cyclopropanecarboxylate

HRID 907464노트

반응식

HRID 907464 반응식
[I-].C[S+](C)(C)=O.[CH3:7]C([O-])(C)C.[K+].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[C:16]=1[C:23](=[CH2:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25].O>CS(C)=O>[CH3:22][O:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH3:13])[C:16]=1[C:23]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:7][CH2:29]1

참가 물질

6

반응물 4

HCID 962WaterHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23665647Potassium tert-butoxideHCID 57659400Ethyl 2-(2,6-dimethoxyphenyl)acrylate

생성물 1

HCID 57659403Ethyl 1-(2,6-dimethoxyphenyl)cyclopropanecarboxylate수율 70%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

To trimethylsulfoxonium iodide (32 g, 1.2 equiv) in DMSO (250 ml) was added ground KOt-Bu (17.62 g, 1.3 equiv) and this mixture was stirred at r.t. for 30 min. A solution of the styrene 17 (28.53 g, 121 mmol) in DMSO (55 ml) was then added and this mixture was stirred at r.t. for 3 h. The reaction was poured into water (1.0 L) mixed with sat. NHCl (350 ml). The product was extracted into hexane (2×300 ml) and this solution was washed with water and brine, dried over Na2SO4 and filtered through silica (400 ml). The product was then eluted with EtOAc/hexane 15 and 20% to yield 18 (21.1 g, 70%) as a colorless oil.

후처리

  1. stirringthis mixture was stirred at r.t. for 3 h
  2. additionmixed with sat. NHCl (350 ml)
  3. extractionThe product was extracted into hexane (2×300 ml)
  4. washthis solution was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered through silica (400 ml)
  7. washThe product was then eluted with EtOAc/hexane 15 and 20%

출처 및 근거

ORD 기록
ord-b292f3a4d9614aaca02030b845a14e3c
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013159B2

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