Sodium borohydride → HCID 68728415, compound

HRID 1892065Notes

Reaction equation

HRID 1892065 reaction equation
[Br:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:13][CH3:14])=[CH:7][C:8]=2[CH3:12])[C:3]1=[O:15].[BH4-].[Na+]>CO>[Br:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:13][CH3:14])=[CH:7][C:8]=2[CH3:12])[CH:3]1[OH:15]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68727096HCID 68727096, compound

Product 1

HCID 68728415HCID 68728415, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the ice-cold solution of 2-bromo-7-methoxy-5-methyl-3,4-dihydro-2H-naphthalen-1-one (10 g, 0.04 mol) obtained in Step 1 in methanol (100 mL) was added sodium borohydride (2.0 g, 0.05 mol) and the mixture was stirred for 2 h at room temperature. The reaction mixture was cooled and quenched with acetone and concentrated. The mixture was diluted with water and extracted in diethyl ether. The organic layer was washed with brine, dried and concentrated to yield the 2-bromo-7-methoxy-5-methyl-1,2,3,4-tetrahydro-naphthalen-1-ol, 8.0 g, which was used as such in Step 3.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched with acetone
  3. concentrationconcentrated
  4. additionThe mixture was diluted with water
  5. extractionextracted in diethyl ether
  6. washThe organic layer was washed with brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d6a6e38ac4114abcb18a024a113c60b3
Source dataset
uspto-grants-2013_08
Patent number
US08507509B2

Reaction notes

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