Citric Acid → HCID 19390047, compound

HRID 2070606Notes

Reaction equation

HRID 2070606 reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[CH2:21][CH2:20][C:13]2([CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]2)[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[Si:1]([O:8][CH2:9][CH:10]1[CH2:21][CH2:20][C:13]2([CH2:14][CH2:15][CH:16]([OH:19])[CH2:17][CH2:18]2)[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 53657024HCID 53657024, compound

Product 1

HCID 19390047HCID 19390047, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 9-(tert-butyldimethylsilanyloxymethyl)-spiro[5.5]undecan-3-one (1.5 g) obtained in Step 3 in methanol (24 mL) was added sodium borohydride (0.17 g) under ice-cooling, followed by stirring the reaction mixture under ice-cooling for 0.5 hour. After addition of saturated aqueous citric acid solution, the reaction mixture was concentrated in vacuo, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:19 to 1:4) to give 9-(tert-butyldimethylsilanyloxymethyl)-spiro[5.5]undecan-3-ol (0.47 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for 0.5 hour
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:19 to 1:4)

Sources & evidence

ORD record
ord-924a335d5f3a4e1bab39301defacafac
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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