HCID 18436340, compound → HCID 18436339, compound

HRID 351442Notes

Reaction equation

[CH2:1]([CH:3]1[CH:8]([CH3:9])[CH:7]([CH2:10][O:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH2:6][C:5](=[O:16])[CH:4]1[C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)[CH3:2]>C1COCC1.[NH4+].[Cl-].C(OCC)(=O)C>[CH2:1]([CH:3]1[CH:8]([CH3:9])[CH:7]([CH2:10][O:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH2:6][C:5]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)([OH:16])[CH:4]1[C:17]1[CH:18]=[CH:19][C:20]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:21][CH:22]=1)[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 3-ethyl-4-methyl-2-(4-phenoxy-phenyl)-5-trimethylsilanyloxymethyl-cyclohexanone (1.8 g, 3.8 mmol) in THF (10 mL) at −10° C. was added Grinard reagent (1.0 M, 7.5 mL). The reaction mixture was stirred at 25° C. for 1 h and then refluxed for 30 min. The reaction mixture was then cooled and diluted with aqueous saturated NH4Cl (100 mL) and ethyl acetate (100 mL). The organic layer was separated, dried over MgSO4 and purified on SiO2 (100% ethyl acetate) to yield crude product 3-ethyl-1-(4-methoxy-phenyl)-4-methyl-2-(4-phenoxy-phenyl)-5-trimethylsilanyloxymethyl-cyclohexanol. NMR showed S: R product ratio or 2:1. Further purification provide pure 3-ethyl-1-(4-methoxy-phenyl)-4-methyl-2-(4-phenoxy-phenyl)-5-trimethylsilanyloxymethyl-cyclohexanol.

Workup

temperaturerefluxed for 30 min
temperatureThe reaction mixture was then cooled
customThe organic layer was separated
dry with materialdried over MgSO4
custompurified on SiO2 (100% ethyl acetate)

Sources & evidence

ORD record: ord-b7a0700f32af4ba6a2e557f1f692cc61
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183445B2

Reaction notes

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