Sodium borohydride → 5-(Benzyloxy)-1-hydroxy-2-(methoxycarbonyl)-1,2,3,4-tetrahydronaphthalene

HRID 1271266Notes

Reaction equation

HRID 1271266 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH:13]([C:20]([O:22][CH3:23])=[O:21])[C:14]2=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH:13]([C:20]([O:22][CH3:23])=[O:21])[CH:14]2[OH:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 229320015-(Benzyloxy)-2-(methoxycarbonyl)-1-tetralone

Product 1

HCID 229319625-(Benzyloxy)-1-hydroxy-2-(methoxycarbonyl)-1,2,3,4-tetrahydronaphthaleneYield 74.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7.95 g of 5-(benzyloxy)-2-(methoxycarbonyl)-1-tetralone in 80 ml of methanol was ice-cooled and 0.97 g of sodium borohydride was added in five portions. After stirring for 30 minutes, an ice bath was removed and the mixture was further stirred for 30 minutes. The reaction solution was diluted with iced water, extracted with diethyl ether, washed with water and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressured. The residue was purified by silica gel column chromatography to obtain 5.96 g of the desired compound as a colorless oily substance.

Workup

  1. temperaturecooled
  2. customan ice bath was removed
  3. stirringthe mixture was further stirred for 30 minutes
  4. additionThe reaction solution was diluted with iced water
  5. extractionextracted with diethyl ether
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressured
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b8caffb593e74adbbac590c7ee342992
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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