Methanol → (S)-(+)-1-Phenyl-1,2-ethanediol

HRID 1525141Notes

Reaction equation

HRID 1525141 reaction equation
C[OH:2].N12CCCN=C1CCCCC2.[CH3:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C[CH:21]([OH:23])[CH3:22]>>[C:16]1([C@H:21]([OH:23])[CH2:22][OH:2])[CH:15]=[CH:14][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 3776IsopropanolHCID 8058HexaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 643312(S)-(+)-1-Phenyl-1,2-ethanediol

Conditions

Temperature
30 °C

Procedure

To a 100 mL autoclave with a stirrer, 2-hydroxyacetophenone (340 mg, 2.5 mmol) and RuCl[(S)-xylbinap][(S)-daipen] obtained from the Example 1 above (1.5 mg, 0.00125 mol, 1/2,000 molar fold of 2-hydroxyacetophenone) were added. After purging with nitrogen, methanol (1.25 mL) and 1,8-diazabicyclo[5.4.0]undeca-7-ene (1.9 mg, 0.0125 mmol) were added. Subsequently, purging with hydrogen, the mixture was stirred at 30° C. for 5 hours under hydrogen pressure of 1 MPa. As a result of analysis of the reaction solution by using gas chromatography (HP-1), the conversion rate was found to be 99% or more. The optical purity was measured by high performance liquid chromatography (CHIRALPAK AS-H, eluent; hexane:2-propanol=92:8), and it was found to be 94% ee.

Workup

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Sources & evidence

ORD record
ord-fc5a83b9db8541fc8a5c3763c17b38f7
Source dataset
uspto-grants-2015_07
Patent number
US09079931B2

Reaction notes

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