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

HRID 639845

反応式

HRID 639845 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

{[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.

後処理

  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)

出典と根拠

ORDレコード
ord-ccfab170865e4aa2a012ddae800d2bfb
出典データセット
uspto-grants-2010_04
特許番号
US07691893B2

関連ノート

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