1-Tetralone → 1-Tetralol, (S)-

HRID 1525140Notes

Reaction equation

[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.CC([O-])(C)C.[K+]>CC(O)C>[C@@H:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a 100 mL autoclave with a stirrer, trans-RuCl2[(R)-dm-segphos][(S)-daiPen] (3.6 mg, 0.003 mol, 1/1,000 molar fold of 1-tetralone) was added. After purging with nitrogen, 2-propanol (3 mL), 1-tetralone (439 mg, 3 mmol) and 2-propanol solution of t-BuOK (0.1 mol/L, 0.3 mL, 0.03 mmol) were added. Subsequently, purging with hydrogen, the mixture was stirred at 25° C. for 15 hours under hydrogen pressure of 1 MPa. As a result of analysis of the reaction solution by using gas chromatography (Chirasil-DEX CB), it was found that the conversion rate is 42% and the optical purity is 90% ee.

Workup

additionwere added
customSubsequently, purging with hydrogen
customAs a result of analysis of the reaction solution

Sources & evidence

ORD record: ord-5c2689ccbf2747d6bc0cc54918bf534b
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079931B2

Reaction notes

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