HCID 22664990, compound → HCID 22664992, compound

HRID 2113684Notes

Reaction equation

[CH2:1]([C:5]1([CH2:22][CH2:23][CH2:24][CH:25]=C)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH2:15][O:16][CH3:17])[CH:11]=2)[C:6]1([C:19]([CH3:21])=[CH2:20])[OH:18])[CH2:2][CH2:3]C>ClCCl.[Ru+2](Cl)Cl>[CH2:22]([C:5]12[CH2:1][CH2:2][CH2:3][CH:21]=[C:19]([CH3:20])[C:6]1([OH:18])[C:7]1[CH:8]=[CH:9][C:10]([O:14][CH2:15][O:16][CH3:17])=[CH:11][C:12]=1[CH2:13]2)[CH2:23][CH2:24][CH3:25]

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of 2-butyl-1-isopropenyl-5-(methoxymethoxy)-2-(4-pentenyl)-1-indanol (200 mg, 0.56 mmol) in dichloromethane (22 mL) was treated with tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydro-imidazol-2-ylidene]benzylidine]ruthenium(IV) dichloride (47 mg, 0.056 mmol). After stirring at 45° C. overnight, the mixture was treated with additional tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydro-imidazol-2-ylidene]benzylidine]ruthenium (IV) dichloride (47 mg, 0.056 mmol) and stirred at 45° C. for another 24 hours. The mixture was concentrated and the residue purified by preparative layer chromatography on two 0.1×20×20 cm silica gel GF plates (Analtech, Newark, Del.), developing with 10% EtOAc in hexane. The UV visible product band was eluted with EtOAc and the eluant was evaporated under vacuum to provide 9a-butyl-2-(methoxymethoxy)-5-methyl-8,9,9a,10-tetrahydrobenzo[a]azulen-4b(7H)-ol as an oil.

Workup

stirringstirred at 45° C. for another 24 hours
concentrationThe mixture was concentrated
customthe residue purified by preparative layer chromatography on two 0.1×20×20 cm silica gel GF plates (Analtech, Newark, Del.)
washThe UV visible product band was eluted with EtOAc
customthe eluant was evaporated under vacuum

Sources & evidence

ORD record: ord-b5349cb801f44bcd95340f8974cf55d6
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432284B2

Reaction notes

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