Acetophenone → 1-Phenylethanol, (R)-

HRID 1773167Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[C:4]1([C@H:1]([OH:3])[CH3:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 30 °C

Procedure

To a 100 mL autoclave with a stirrer bar, acetophenone (1.2 g, 10 mmol) and {Ru[(S)-daipena][(S)-xylbinap]}PF6 obtained from Example 2 above (12.9 mg, 0.01 mmol, 1/1000 molar fold of acetophenone) were added. After purging with a nitrogen gas, toluene (5 mL) and 1,8-diazabicyclo[5,4,0]undeca-7-ene (15.2 mg, 0.1 mmol) were added thereto. Subsequently, purging with a hydrogen gas, the mixture was stirred at 30° C. for 3 hours under hydrogen pressure 1 MPa. As a result of analysis of the reaction mixture by gas chromatography (Chirasil-DEX CB), it was found that the conversion rate is 99.6% and optical purity is 99.6% ee.

Workup

additionwere added
customSubsequently, purging with a hydrogen gas
customAs a result of analysis of the reaction mixture by gas chromatography (Chirasil-DEX CB), it

Sources & evidence

ORD record: ord-f292bd9033b746e08fc40c46faf0b641
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255049B2

Reaction notes

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