4'-Fluoroacetophenone → HCID 178466805, compound

HRID 1162558Notes

Reaction equation

HRID 1162558 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1.[H-].[Na+].F[C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=1>CN(C=O)C>[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([O:8][C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 98284'-FluoroacetophenoneHCID 24758Sodium hydrideHCID 178461406HCID 178461406, compound

Product 1

HCID 178466805HCID 178466805, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

cis-4-Methyl-cyclohexanol (3.28 g, 28.7 mmol), NaH (1.09 g, 27.3 mmol, 60% suspension in mineral oil) and DMF (50 mL) were combined and sonicated as in general procedure L. The mixture was charged with 4′-fluoroacetophenone (2.18 mL, 17.8 mmol) and heated. After aqueous workup, the crude residue was purified on a silica gel column (gradient, hexane→2% EtOAc-hexane) to obtain 1-[4-(cis-4-Methyl-cyclohexyloxy)-phenyl]-ethanone (976 mg).

Workup

  1. customsonicated as in general procedure L
  2. temperatureheated
  3. customAfter aqueous workup, the crude residue was purified on a silica gel column (gradient, hexane→2% EtOAc-hexane)

Sources & evidence

ORD record
ord-8ae9faf48a0f443fa1f5a923e8a76d15
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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