Sodium borohydride → 1-(4-Bromo-3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanol

HRID 2180593Notes

Reaction equation

HRID 2180593 reaction equation
[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:14](=[O:16])[CH3:15])[C:3]=1[O:17][CH3:18].[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([CH:14]([OH:16])[CH3:15])[C:3]=1[O:17][CH3:18]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 224910531-(4-Bromo-3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl) ethanone

Product 1

HCID 224909511-(4-Bromo-3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(4-bromo-3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (Compound A-93, 12.1 g, 39 mmol) in ethanol (250 mL) was added sodium borohydride (741 mg, 19.5 mmol). After heating to reflux for 2 h the mixture was cooled to room temperature, quenched with 10% HCl and extracted with diethyl ether. The combined ethereal layers were washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a colorless syrup. The material was used in the next step without further purification.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 2 h the mixture
  3. customquenched with 10% HCl
  4. extractionextracted with diethyl ether
  5. washThe combined ethereal layers were washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d8c71b7f89f64ce1a492d296a01876e4
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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