2-Cyclohexen-1-one → (R)-3-Phenylcyclohexanone

HRID 1470768Notes

Reaction equation

HRID 1470768 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[C:8]1(B(O)O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O>[C:8]1([C@@H:3]2[CH2:4][CH2:5][CH2:6][C:1](=[O:7])[CH2:2]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 135942-Cyclohexen-1-oneHCID 66827Phenylboronic Acid

Product 1

HCID 11041212(R)-3-PhenylcyclohexanoneYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cyclohexenone (30 mg, 0.312 mmol), a rhodium complex of Rh(acac) (C2H4)2 (5.2 mg, 0.02 mmol), 50 mg of the polymer having the (R)-BINAP group (17) obtained in Preparation Example 1 and a phenylboronic acid (244 mg, 2.0 mmol) were reacted in 4 mL of water at 100° C. for 13 hours. The reaction mixture was filtered out to recover the polymer having the (R)-BINAP group. Meanwhile, the filtrate was extracted with ether and washed with saturated sodium hydrogen carbonate aqueous solution and saturated saline. It was dried over sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by preparative chromatography (hexyane:ethyl acetate=3:1) to obtain 43.5 mg of (R)-3-phenylcyclohexanone with optical purity of 97% ee in 80% yield.

Workup

  1. customobtained in Preparation Example 1
  2. filtrationThe reaction mixture was filtered out
  3. customto recover the polymer
  4. extractionMeanwhile, the filtrate was extracted with ether
  5. washwashed with saturated sodium hydrogen carbonate aqueous solution and saturated saline
  6. dry with materialIt was dried over sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customto obtain a crude product
  9. customThe crude product was purified by preparative chromatography (hexyane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-c3f9e78388ea4403bcb386707d87b62c
Source dataset
uspto-grants-2015_04
Patent number
US09006484B2

Reaction notes

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