Diethyl fumarate → Diethyl 4-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)cyclohex-4-ene-1,2-dicarboxylate

HRID 2245238Notes

Reaction equation

HRID 2245238 reaction equation
[C:1]([Si:5]([O:8]/[C:9](=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)/[CH:10]=[CH2:11])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[C:20]([O:29][CH2:30][CH3:31])(=[O:28])/[CH:21]=[CH:22]/[C:23]([O:25][CH2:26][CH3:27])=[O:24]>>[Si:5]([O:8][C:9]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:21]([C:20]([O:29][CH2:30][CH3:31])=[O:28])[CH:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:11][CH:10]=1)([C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:7])[CH3:6]

Participants

3

Reactant 2

HCID 638144Diethyl fumarateHCID 210993091Z-tert-butyl{[1-(4-fluorobenzylidene)prop-2-en-1-yl]oxy}dimethylsilane

Product 1

HCID 68541249Diethyl 4-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)cyclohex-4-ene-1,2-dicarboxylate

Procedure

To a solution of 37 g (˜80% pure, 133.1 mmol, 1 equiv.) of 1E and 1Z-tert-butyl{[1-(4-fluorobenzylidene)prop-2-en-1-yl]oxy}dimethylsilane (intermediate step C) and 17 mL (18 g, 104.6 mmol) diethyl (2E)-but-2-enedioate in 200 mL xylenes under nitrogen atmosphere was heated at 160° C. for 5 hr then cooled to RT. The solvent was evaporated under vacuum to give an oil which was used without further purification.

Workup

  1. customThe solvent was evaporated under vacuum
  2. customto give an oil which
  3. customwas used without further purification

Sources & evidence

ORD record
ord-70a007ef55124a6abbeb5653c59a6322
Source dataset
uspto-grants-2010_03
Patent number
US07683068B2

Reaction notes

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