Ethanol → Tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenylsilane

HRID 1862760Notes

Reaction equation

HRID 1862760 reaction equation
[CH2:1]([O:8][C:9]1[CH:32]=[CH:31][C:12]([O:13][Si:14]([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=CC=CC=1.C1CCCCC=1.C([OH:41])C>[Pd]>[C:27]([Si:14]([O:13][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][CH:2]2[CH2:7][O:41]2)=[CH:32][CH:31]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:28])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 702EthanolHCID 8079CyclohexeneHCID 5326061-Benzyloxy-4-diphenyl(tert-butyl)silyloxybenzene

Product 1

HCID 12045564Tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenylsilane

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(4-Benzyloxy-phenoxy)-tert-butyl-diphenyl-silane (32.5 g, 67 mmol) was dissolved in ethanol. 10% Palladium on carbon (3.0 g) was added followed by cyclohexene (100 mL). The mixture was heated at reflux for 16 hours. The reaction was cooled to room temperature and filtered through Celite. The solvent was removed in vacuo to yield the title compound (22.0 g, 63 mmol).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 hours
  3. filtrationfiltered through Celite
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-97d28f0209dc4541b0b63303345470fe
Source dataset
uspto-grants-2003_03
Patent number
US06537994B2

Reaction notes

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