Hexane → 3-Fluoro-4-(2-phenylethoxy)cyclohexanol

HRID 271379Notes

Reaction equation

HRID 271379 reaction equation
C([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][CH2:16][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=O)[CH:11]([F:25])[CH2:10]1)C1C=CC=CC=1.CCCCCC>[Pd].C(OCC)(=O)C>[F:25][CH:11]1[CH:12]([O:15][CH2:16][CH2:17][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][CH2:14][CH:9]([OH:8])[CH2:10]1

Participants

5

Reactant 2

HCID 8058HexaneHCID 692747802-{[4-(Benzyloxy)-2-fluorocyclohexyl]oxy}-1-phenylethanone

Product 1

HCID 692763363-Fluoro-4-(2-phenylethoxy)cyclohexanolYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To an ethyl acetate (100 mL) solution of (−) 2-{[4-(Benzyloxy)-2-fluorocyclohexyl]oxy}-1-phenylethanone (1.44 g, 4.18 mmol) was added 10% palladium on carbon (0.200 g). The resulting mixture was hydrogenated using a balloon. After 20 h the contents of the reaction flask were filtered through celite® and the filtrate evaporated under reduced pressure. Flash column chromatography (hexane:ethyl acetate, 60:40) gave 3-Fluoro-4-(2-phenylethoxy)cyclohexanol as a colorless oil (0.918 g, 92% yield).

Workup

  1. filtrationAfter 20 h the contents of the reaction flask were filtered through celite®
  2. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-c3f27caa1bb244e090a8bd9069c8b6ee
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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