2,3-Dihydro-1H-cyclopenta[a]naphthalen-1-one → HCID 10103867, compound

HRID 1585966Notes

Reaction equation

HRID 1585966 reaction equation
[C:1]1(=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]3=2)[CH2:3][CH2:2]1.[BH4-].[Na+]>C1COCC1.CO>[CH:1]1([OH:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]3=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 2404542,3-Dihydro-1H-cyclopenta[a]naphthalen-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 10103867HCID 10103867, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 12.36 g portion of benzindanone (63 mmole) was dissolved in 300 ml of THF and 150 ml of methanol, and 3.6 g (95 mmole) of sodium borohydride was added at room temperature. After stirring the mixture for 6 hours, the reaction was terminated with dilute hydrochloric acid, and extracted with hexane (100 ml X 2) and ether (100 ml×2). Two stereoisomers of benzindanol were obtained. The crude product was used for the next reaction without purification.

Workup

  1. customthe reaction was terminated with dilute hydrochloric acid
  2. extractionextracted with hexane (100 ml X 2) and ether (100 ml×2)

Sources & evidence

ORD record
ord-271fef6bd4ea4967ba88e29f3dc3b570
Source dataset
uspto-grants-1999_08
Patent number
US05942459

Reaction notes

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