HCID 58596769, compound → HCID 68636763, compound

HRID 1714712Notes

Reaction equation

HRID 1714712 reaction equation
[CH2:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[CH:8][CH:7]=1)[CH:2]=[CH2:3]>ClCCl.C(P(C1CCCCC1)(C1CCCCC1)C1CCCCC1)(P(C1CCCCC1)(C1CCCCC1)C1CCCCC1)C1C=CC=CC=1.Cl[Ru]Cl>[Si:14]([O:13][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][O:4][CH2:1][CH:2]=[CH:3][CH2:1][O:4][CH2:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[CH:8][CH:7]=2)=[CH:11][CH:10]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16]

Participants

4

Reactant 1

HCID 58596769HCID 58596769, compound

Product 1

HCID 68636763HCID 68636763, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 90332616Dichlororuthenium;tricyclohexyl-[phenyl-(tricyclohexyl-lambda5-phosphanyl)methyl]-lambda5-phosphaneCatalystHCID 6344DichloromethaneSolvent

Procedure

Benzylidene-bis(tricyclohexylphosphine)-dichlororuthenium (420 mg, 0.513 mmol, 15 mol %) is added under an argon atmosphere to a solution of 4-allyloxymethyl-1-tert-butyldimethylsilyloxymethyl)-benzene (80, 1.0 g, 3.24 mmol) in 70 mL dry dichloromethane. The reaction mixture is stirred at room temperature for 15 h, and additional catalyst (200 mg) is added and the reaction mixture heated to reflux for 5 h. The solvent is removed in vacuo, and the product purified by column chromatography (petrol ether/ethyl acetate 50:1) to yield 520 mg (0.93 mmol, 55%) of the title compound.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 5 h
  3. customThe solvent is removed in vacuo
  4. customthe product purified by column chromatography (petrol ether/ethyl acetate 50:1)

Sources & evidence

ORD record
ord-243a44dabb0443fb9263f6d9068e4661
Source dataset
uspto-grants-2010_09
Patent number
US07799524B2

Reaction notes

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