(2-(1-Cycloocten-1-yl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanol → (2-Cyclooctyl-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanol

HRID 1662396Notes

Reaction equation

HRID 1662396 reaction equation
[C:1]1([C:9]2[CH:14]=[C:13]([CH2:15][OH:16])[CH:12]=[CH:11][C:10]=2[C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=2[F:25])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>CCOC(C)=O.[Pd]>[CH:1]1([C:9]2[CH:14]=[C:13]([CH2:15][OH:16])[CH:12]=[CH:11][C:10]=2[C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=2[F:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 1

HCID 67360376(2-(1-Cycloocten-1-yl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanol

Product 1

HCID 57706668(2-Cyclooctyl-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanolYield 38%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 66.16E (0.387 g, 1 mmol) in EtOAc (11 mL) at 23° C. was added palladium on carbon (0.1 g, 1 mmol). The reaction was placed under an atmosphere of hydrogen and stirred for 2 hours. The reaction mixture was then filtered and concentrated in vacuo. The residue was purified on silica gel (0-20% EtOAc in hexanes) to yield 66.16F as a colorless oil (0.13 g, 33% yield).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a2caf2f455704478be8b568477984cf2
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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