Benzaldehyde → 1,3-diphenyl-3-hydroxy-2-methyl-1-propanone

HRID 1836946Notes

Reaction equation

HRID 1836946 reaction equation
C(Cl)Cl.[CH:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:12]1([C:18]([O:21][Si](C)(C)C)=[CH:19][CH3:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(O)=O.[Na+]>C(OCC)(=O)C.O.CC(O)C>[C:12]1([C:18](=[O:21])[CH:19]([CH3:20])[CH:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[OH:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 54540068Trimethyl[(1-phenylprop-1-en-1-yl)oxy]silane

Product 1

HCID 101986511,3-diphenyl-3-hydroxy-2-methyl-1-propanoneYield 89%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21889133Propan-2-ol--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

From the methylene chloride solution of the chiral lead catalyst thus prepared, the solvent was evaporated, then dissolved in H2O-i-PrOH (1:4.5, 0.50 ml). After cooling at 0° C., H2O:i-PrOH (1:4.5, 1.0 ml) solutions of benzaldehyde (0.5 mmols) and 1-phenyl-1-trimethylsiloxy-1-propene (0.75 mmols) were added consecutively. After stirring for 20 hours, ethyl acetate (15 ml) and aqueous saturated NaHCO3 solution (10 ml) were added thereto to separate the organic layer, followed by the extraction of the product with ethyl acetate (10 ml×2). The resulting organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated away under reduced pressure, and the residue was purified through thin-layer silica gel chromatography to obtain 1,3-diphenyl-3-hydroxy-2-methyl-1-propanone (89%, syn:anti=91:9, 69% ee (syn)).

Workup

  1. customthe solvent was evaporated
  2. dissolutiondissolved in H2O-i-PrOH (1:4.5, 0.50 ml)
  3. customto separate the organic layer
  4. extractionfollowed by the extraction of the product with ethyl acetate (10 ml×2)
  5. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. customthe residue was purified through thin-layer silica gel chromatography

Sources & evidence

ORD record
ord-fc410f249bc74cb28469f99c23113729
Source dataset
uspto-grants-2004_08
Patent number
US06780812B2

Reaction notes

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