Sodium Hydroxide → HCID 57771565, compound

HRID 2070561Notes

Reaction equation

HRID 2070561 reaction equation
[CH3:1][C:2]1([CH3:15])[C:7]2([CH2:12][CH:11]([CH:13]=[O:14])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH2:4][CH2:3]1.[BH4-].[Na+].[OH-].[Na+]>CO>[CH3:1][C:2]1([CH3:15])[C:7]2([CH2:12][CH:11]([CH2:13][OH:14])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 57771614HCID 57771614, compound

Product 1

HCID 57771565HCID 57771565, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 11,11-dimethyl-spiro[5.5]undec-7-ene-2-carbaldehyde (195 mg) obtained in Step 7 in methanol (5 mL) was added sodium borohydride (55 mg) under ice-cooling, followed by stirring the reaction mixture under ice-cooling for 15 minutes. Then, after addition of 0.5N aqueous sodium hydroxide solution (10 mL), the reaction mixture was extracted with diethyl ether. The organic layer was washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=10:1 to 5:1) to give (11,11-dimethyl-spiro[5.5]undec-7-en-2-yl)-methanol (190 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling for 15 minutes
  3. extractionthe reaction mixture was extracted with diethyl ether
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=10:1 to 5:1)

Sources & evidence

ORD record
ord-e5e4788016154b5cbf702cee7cdb6f0c
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

Loading…