Chromanone → (R)-4-Chromanol

HRID 1505745Notes

Reaction equation

HRID 1505745 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[H][H]>CO>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C@H:4]([OH:11])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 68110ChromanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 640695(R)-4-Chromanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In a 50-ml autoclave, 3.3 mg (0.005 mmol, S/C=1000) of RuCl(R,R)—O-HT-Tsdpen) was placed, and the autoclave was purged with nitrogen. Subsequently, 0.74 g (5.0 mmol) of 4-chromanone and 4.4 ml of methanol were added thereto, and the pressure was raised with hydrogen up to 3.0 MPa. Subsequently, the mixture was stirred for 18 hours at 60° C. The reaction liquid was subjected to a GC analysis, and as a result, (R)-4-chromanol was obtained at a conversion rate of 98.6% with an optical purity of 99.1% ee.

Workup

  1. customthe autoclave was purged with nitrogen
  2. customThe reaction liquid

Sources & evidence

ORD record
ord-54c0c15d01624a13a34c72bab2bdebda
Source dataset
uspto-grants-2015_12
Patent number
US09217005B2

Reaction notes

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