Acetone → HCID 14989156, compound

HRID 484177Notes

Reaction equation

HRID 484177 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:16][CH2:17][CH2:18][C:19](=[O:21])[CH3:20])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].[BH4-].[Na+].CC(C)=O>C(O)C>[CH3:13][C:12]([C:9]1[CH:8]=[C:7]([S:16][CH2:17][CH2:18][CH:19]([OH:21])[CH3:20])[CH:6]=[C:5]([C:2]([CH3:4])([CH3:3])[CH3:1])[C:10]=1[OH:11])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 14989148HCID 14989148, compound

Product 1

HCID 14989156HCID 14989156, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

The title ketone of Example 3 (1.0 g, 0.0032 mole) was dissolved in 10 ml of absolute ethanol and the solution cooled to about 0° C. in an ice bath and 31 mg of sodium borohydride was added. The reaction wa stirred for about one hour and acetone was added. The solvents were removed in vacuo, the residue extracted twice with benzene, the organic extracts combined and dried over sodium sulfate. Removal of the solvent in vacuo gave the crude product which was chromatographed on silica to give the title compound.

Workup

  1. customThe solvents were removed in vacuo
  2. extractionthe residue extracted twice with benzene
  3. dry with materialdried over sodium sulfate
  4. customRemoval of the solvent in vacuo
  5. customgave the crude product which
  6. customwas chromatographed on silica

Sources & evidence

ORD record
ord-4f8ad622995b4ab381c90cff2a51d5e3
Source dataset
uspto-grants-1993_07
Patent number
US05229421

Reaction notes

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