Potassium Hydroxide → Fenipentol

HRID 1855138Notes

Reaction equation

HRID 1855138 reaction equation
[C:1]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[K+]>C1(C)C(C)=CC=CC=1.CO>[C:7]1([CH:1]([OH:6])[CH2:2][CH2:3][CH2:4][CH3:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 66093Valerophenone

Product 1

HCID 3338Fenipentol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7237O-XyleneSolvent2×

Conditions

Temperature
140 °C

Procedure

Tris(triphenylphosphine)ruthenium (II) chloride (1.9 mg, 2 μmol, 0.5 mol %) and a chiral ligand (M=Ru, R=i-Pr, Ar=C6H5—, 1.3 μmol, 0.33 mol %) were dissolved in xylene (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 140° C. After the mixture was cooled to room temperature, pentanophenone (0.4 mmol), xylene (2 mL) and a solution of potassium hydroxide in methanol (0.4 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 12 h under H2 (10 atm) at 25° C. The solvent was removed under reduced pressure, and the resultants were separated by column chromatography (silica gel column; eluent:ethyl acetate/petroleum ether=1/8). Accordingly, pure 1-phenylpentanol was obtained and the ee value (ee=99.6%) was measured by GC analysis.

Workup

  1. temperatureheated
  2. temperatureAfter the mixture was cooled to room temperature
  3. stirringstirred for 12 h under H2 (10 atm) at 25° C
  4. customThe solvent was removed under reduced pressure
  5. customthe resultants were separated by column chromatography (silica gel column; eluent:ethyl acetate/petroleum ether=1/8)

Sources & evidence

ORD record
ord-aa2eaa018d994e91a06471ccb459b1e3
Source dataset
uspto-grants-2015_02
Patent number
US08962852B2

Reaction notes

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