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

HRID 1991358Notes

Reaction equation

HRID 1991358 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([Si](O/C(=C\C1C=CC(F)=CC=1)/C=C)(C)C)(C)(C)C.[C:39]([O:48][CH2:49][CH3:50])(=[O:47])/[CH:40]=[CH:41]/[C:42]([O:44][CH2:45][CH3:46])=[O:43]>>[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:40]([C:39]([O:48][CH2:49][CH3:50])=[O:47])[CH:41]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:11][CH:10]=1)([C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:7])[CH3:6]

Participants

4

Reactant 3

HCID 638144Diethyl fumarateHCID 210993091Z-tert-butyl{[1-(4-fluorobenzylidene)prop-2-en-1-yl]oxy}dimethylsilaneHCID 73742632Tert-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 (Example 1, 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-40c9f9ba635142fe94068e3355cd9c80
Source dataset
uspto-grants-2010_01
Patent number
US07645790B2

Reaction notes

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