Sodium borohydride → HCID 67247455, compound

HRID 1192459Notes

Reaction equation

HRID 1192459 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].[BH4-].[Na+]>CO>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:12]([OH:14])[CH3:13]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13419512HCID 13419512, compound

Product 1

HCID 67247455HCID 67247455, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 1-(1-bromo-2-naphthyl)ethanone (0.488 g, 1.96 mmol) in methanol (10 mL) was added sodium tetrahydroborate (0.0741 g, 1.96 mmol). The reaction was stirred at room temperature for 30 minutes, quenched with water, extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated to dryness under reduced pressure. The residue was used directly in next step (467 mg, 94%). LCMS calculated for C12H10Br(M−OH)+: m/z=233.0; found: 233.2.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a6e6a892f7614ae18657c36d1876f738
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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