HCID 86677003, compound → HCID 78058497, compound

HRID 2096126Notes

Reaction equation

HRID 2096126 reaction equation
CC(=C[CH2:5][CH2:6][CH:7]([CH3:22])[CH2:8][C:9](=[O:21])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20])C>Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1.ClCCl>[CH3:22][CH:7]1[CH2:6][CH2:5][CH:20]=[CH:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9](=[O:21])[CH2:8]1

Participants

4

Reactant 1

HCID 86677003HCID 86677003, compound

Product 1

HCID 78058497HCID 78058497, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Grubbs' Catalyst, 2nd generation (benzylidene [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene] dichloro (tricyclohexylphosphine) ruthenium) (560 mg, 0.066 mmol, 2 mol %), was added to a solution of 2,6-dimethyl-nonadeca-2,18-dien-8-one (1 g, 3.3 mmol, prepared as above in Example IV) in dichloromethane at room temperature. The reaction mixture was stirred at reflux for 12 hours. The reaction mixtures was subsequently concentrated and then chromatographed on silica with ethyl acetate in hexanes (2%) as the eluent providing 3-methyl-cyclohexadec-6-enone as a colorless oil (0.4 g). This oil was then filtered through a slurry of silica gel/activated charcoal.

Workup

  1. temperatureat reflux for 12 hours
  2. customThe reaction mixtures
  3. concentrationwas subsequently concentrated
  4. customchromatographed on silica with ethyl acetate in hexanes (2%) as the eluent

Sources & evidence

ORD record
ord-d6c6b52c587341599fe6d54b3600d5be
Source dataset
uspto-grants-2013_05
Patent number
US08450265B2

Reaction notes

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