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

HRID 639845

Reaction equation

[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]

Participants

Conditions

Temperature: 100 °C

Procedure

{[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.

Workup

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

Sources & evidence

ORD record: ord-ccfab170865e4aa2a012ddae800d2bfb
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691893B2

Linked notes

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