Sodium borohydride → 5,7-Dimethyl-8-methoxy-9-hydroxy-1,2,3,4,4a,9a-hexahydrofluorene

HRID 2051417Notes

Reaction equation

HRID 2051417 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH:16]=[C:15]([CH3:17])[C:14]([O:18][CH3:19])=[C:13]2[C:5]=1[CH:6]1[CH:11]([C:12]2=[O:20])[CH2:10][CH2:9][CH2:8][CH2:7]1>CO.O>[CH3:3][C:4]1[CH:16]=[C:15]([CH3:17])[C:14]([O:18][CH3:19])=[C:13]2[C:5]=1[CH:6]1[CH:11]([CH:12]2[OH:20])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 140437135,7-Dimethyl-8-methoxy-1,2,3,4,4a,9a-hexahydro-9-fluorenone

Product 1

HCID 151571985,7-Dimethyl-8-methoxy-9-hydroxy-1,2,3,4,4a,9a-hexahydrofluoreneYield 106.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

6.0 Grams of sodium borohydride was added to a solution prepared by dissolving 15.0 g of 5,7-dimethyl-8-methoxy-1,2,3,4,4a,9a-hexahydro-9-fluorenone in 300 ml of methanol and 50 ml of water and reaction was effected under ice-cooling for 4 hours. The solvent was distilled off and the residue was extracted with dichloromethane and then the extract was washed twice with saturated sodium chloride solution. Then, this was dried with magnesium sulfate and the solvent was distilled off to obtain 16.1 g of 5,7-dimethyl-8-methoxy-9-hydroxy-1,2,3,4,4a,9a-hexahydrofluorene.

Workup

  1. customprepared
  2. dissolutionby dissolving
  3. temperaturecooling for 4 hours
  4. distillationThe solvent was distilled off
  5. extractionthe residue was extracted with dichloromethane
  6. washthe extract was washed twice with saturated sodium chloride solution
  7. dry with materialThen, this was dried with magnesium sulfate
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-65580a5888274b07abe19339203365b3
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

Loading…