Acetone → HCID 70231797, compound

HRID 2371488Notes

Reaction equation

HRID 2371488 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH:21]=[O:22].[BH4-].[Na+].CC(C)=O>C(O)C.C1COCC1.[Cl-].[Na+].O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][OH:22]

Participants

7

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 88223057HCID 88223057, compound

Product 1

HCID 70231797HCID 70231797, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of the aldehyde from Step 2 (1.0 g, 3.2 mmol) in ethanol (50 mL) and THF (20 mL) there was added cerous chloride (0.79 g, 3.2 mmol) and sodium borohydride (0.13 g, 3.5 mmol). The mixture was stirred at room temperature for 30 minutes, there was added acetone (3 mL) and after 5 minutes the mixture was diluted with brine (100 mL) and extracted with ether (100 mL). The crude material was purified by column chromatography on silica gel, eluting with a 1:5 mixture of ethyl acetate-hexane to afford the title compound as a thick yellow oil.

Workup

  1. extractionextracted with ether (100 mL)
  2. customThe crude material was purified by column chromatography on silica gel
  3. washeluting with a 1:5 mixture of ethyl acetate-hexane

Sources & evidence

ORD record
ord-3fd63174055b4954904ebbd85a6736e2
Source dataset
uspto-grants-1992_03
Patent number
US05093356

Reaction notes

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