HCID 69274730, compound → HCID 69275924, compound

HRID 271384Notes

Reaction equation

HRID 271384 reaction equation
C([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][CH2:16][CH:17]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH:11]([F:32])[CH2:10]1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[Si:19]([O:18][CH:17]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH2:16][O:15][CH:12]1[CH2:13][CH2:14][CH:9]([OH:8])[CH2:10][CH:11]1[F:32])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 69274730HCID 69274730, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69275924HCID 69275924, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-{[4-(Benzyloxy)-2-fluorocyclohexyl]oxy}-1-phenylethoxy)(tert-butyl)dimethylsilane (11.3 g, 24.7 mmol) in ethyl acetate (200 mL) was added 10% Pd/C (1.0 g) at room temperature. The reaction mixture was stirred under balloon pressure hydrogen for 4 h, filtered and concentrated. Purification by silica gel chromatography (hexane: ethyl acetate 60:40) gave 4-(2-{[tert-Butyl(dimethyl)silyl]oxy}-2-phenylethoxy)-3-fluorocyclohexanol (8.46 g, 93% yield) as a clear oil.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customPurification by silica gel chromatography (hexane: ethyl acetate 60:40)

Sources & evidence

ORD record
ord-1722ac4009c64db5a55c969221a8302a
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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