1-Tetralone → (R)-(-)-1,2,3,4-Tetrahydro-1-naphthol

HRID 1505746Notes

Reaction equation

HRID 1505746 reaction equation
[CH2:1]1[CH2:11][C:9](=[O:10])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.[H][H]>CO>[CH2:1]1[CH2:2][C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[C@H:9]([OH:10])[CH2:11]1

Participants

4

Reactant 2

HCID 107241-TetraloneHCID 178418361HCID 178418361, compound

Product 1

HCID 7058028(R)-(-)-1,2,3,4-Tetrahydro-1-naphthol

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, 0.73 g (5.0 mmol) of α-tetralone and 4.4 ml of methanol were added thereto, then hydrogen gas was charged to 3.0 MPa. Subsequently, the mixture was stirred for 20 hours at 60° C. The reaction liquid was subjected to a GC analysis, and as a result, (R)-1-tetralol was obtained at a conversion rate of 52.0% with an optical purity of 99.3% ee.

Workup

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

Sources & evidence

ORD record
ord-9e1619e5fdec4a0fb3d5b331b51739e9
Source dataset
uspto-grants-2015_12
Patent number
US09217005B2

Reaction notes

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