HCID 86677003, compound → HCID 78058497, compound

HRID 537390Notes

Reaction equation

HRID 537390 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-666fedb5421b425e9abc1be84fc953a2
Source dataset
uspto-grants-2014_10
Patent number
US08859820B1

Reaction notes

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