Acetate → Dimethyl 2-(3,4-dichlorophenyl)-2-(2-{[(1,1-dimethylethyl)(diphenyl)silyl]oxy}ethyl)-1,1-cyclopropanedicarboxylate

HRID 639845

반응식

HRID 639845 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[CH2:30])[CH2:10][CH2:11][O:12][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[N+](=[C:33]([C:38]([O:40][CH3:41])=[O:39])[C:34]([O:36][CH3:37])=[O:35])=[N-].C([O-])(=O)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:10][CH2:11][O:12][Si:13]([C:26]([CH3:27])([CH3:29])[CH3:28])([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:30][C:33]2([C:38]([O:40][CH3:41])=[O:39])[C:34]([O:36][CH3:37])=[O:35])[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

5

반응물 3

HCID 175AcetateHCID 5476732-Diazonio-1,3-dimethoxy-3-oxoprop-1-en-1-olateHCID 59255999{[3-(3,4-Dichlorophenyl)-3-buten-1-yl]oxy}(1,1-dimethylethyl)diphenylsilane

생성물 1

HCID 59256005Dimethyl 2-(3,4-dichlorophenyl)-2-(2-{[(1,1-dimethylethyl)(diphenyl)silyl]oxy}ethyl)-1,1-cyclopropanedicarboxylate수율 82.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

{[3-(3,4-Dichlorophenyl)-3-buten-1-yl]oxy}(1,1-dimethylethyl)diphenylsilane (P13, 2.25 g), dimethyl diazopropanedioate (1.2 g) (prepared in an analogous manner as reported in Synthetic Communications, 17(4), 1709-16, 1987) and rodhium (II) acetate dimer (0.060 g) were mixed together and heated at 100° C. for 40 min. After cooling, the residue was treated with DCM and the mixture was filtered. The filtrate was evaporated under reduced pressure and the crude product was purified by flash chromatography (Cy/EA from 1/0 to 95/5) to give the title compound (2.38 g) as a colourless oil.

후처리

  1. additionwere mixed together
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. customThe filtrate was evaporated under reduced pressure
  5. customthe crude product was purified by flash chromatography (Cy/EA from 1/0 to 95/5)

출처 및 근거

ORD 기록
ord-ccfab170865e4aa2a012ddae800d2bfb
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691893B2

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