Butyrophenone → HCID 11819186, compound

HRID 1855137Notes

Reaction equation

HRID 1855137 reaction equation
[C:1]1([C:7](=[O:11])[CH2:8][CH2:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)(C)C.C1C=CC=CC=1.C1C=CC=CC=1.Cl[Ru]Cl.Cl[Ru]Cl>[C:1]1([CH:7]([OH:11])[C:8]#[C:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 10315ButyrophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 11819186HCID 11819186, compound

Reagents, catalysts & solvents 2

HCID 10962144Benzeneruthenium(II) Chloride DimerCatalystHCID 3776IsopropanolSolvent3×

Conditions

Temperature
85 °C

Procedure

Benzeneruthenium(II) chloride dimer (1.0 mg, 2 μmol, 0.5 mol %) and a chiral ligand (M=Ru, R=t-Bu, Ar=3,5-t-Bu2C6H3—, 2.6 μmol, 0.65 mol %) were dissolved in i-propanol (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 85° C. After the mixture was cooled to room temperature, 1-phenylbutan-1-one (0.4 mmol), i-propanol (2 mL) and a solution of sodium hydroxide in i-propanol (0.4 mL, 0.4 M) were added thereto. Thereafter, the reaction system were placed in an autoclave, and stirred for 12 h under H2 (10 atm) at 40° 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-phenylbutynol was obtained and the ee value (ee=99.2%) 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 40° 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-dcdf5757de164be3b7b97df52b2bdb36
Source dataset
uspto-grants-2015_02
Patent number
US08962852B2

Reaction notes

Loading…