Sodium borohydride → 3-Phenylcyclopentan-1-ol

HRID 1696273Notes

Reaction equation

HRID 1696273 reaction equation
[C:1]1([CH:7]2[CH2:11][CH2:10][C:9](=[O:12])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:1]1([CH:7]2[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 111374333-Phenylcyclopentan-1-one

Product 1

HCID 2756203-Phenylcyclopentan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-phenylcyclopentanone (1.3 g, 8.12 mmol) and NaBH4 (0.61 g, 16.24 mmol) in methanol (15 mL) was stirred at room temperature for 1 h. The mixture was concentrated, dissolved in CH2Cl2, washed with 10% HCl, brine, dried over MgSO4 and concentrated to afford the title compound as a white solid. MS m/z: 163 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in CH2Cl2
  3. washwashed with 10% HCl, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-00046492f7684a9ca2cf9c45a51bcc05
Source dataset
uspto-grants-2012_04
Patent number
US08163766B2

Reaction notes

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