E-{5-Fluoro-2-[2-(4-methoxyphenyl)vinyl]phenyl}methanol → {5-Fluoro-2-[2-(4-methoxyphenyl)ethyl]phenyl}methanol

HRID 1672632Notes

Reaction equation

HRID 1672632 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:6]([CH2:8][OH:9])[CH:7]=1>[Pd].CO.C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)=[C:6]([CH2:8][OH:9])[CH:7]=1

Participants

5

Reactant 1

HCID 57831377E-{5-Fluoro-2-[2-(4-methoxyphenyl)vinyl]phenyl}methanol

Product 1

HCID 57831395{5-Fluoro-2-[2-(4-methoxyphenyl)ethyl]phenyl}methanolYield 87%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 6.8 g (26.33 mmol) of E-{5-fluoro-2-[2-(4-methoxyphenyl)vinyl]phenyl}methanol from Example 30A and 0.5 g of palladium on carbon (10%) in 50 ml of methanol and 250 ml of ethanol is hydrogenated under atmospheric pressure at room temperature for 1 hour. After reaction has stopped, the mixture is filtered through kieselguhr and the filtrate is then concentrated to dryness. The residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→4:1→1:1). 5.95 g (87% yield) of a colorless solid are obtained.

Workup

  1. customAfter reaction
  2. filtrationthe mixture is filtered through kieselguhr
  3. concentrationthe filtrate is then concentrated to dryness
  4. customThe residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→4:1→1:1)

Sources & evidence

ORD record
ord-2b21a2707c4347f4981a5eb5c9e43db8
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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