Water → HCID 17825607, compound

HRID 1297043Notes

Reaction equation

HRID 1297043 reaction equation
[Cr](O)(O)(=O)=O.S(=O)(=O)(O)O.[OH2:11].[OH:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17][C:18](=[O:38])[CH2:19][C:20]([O:22][CH2:23][CH2:24][CH:25]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:21]>CC(C)=O.C(OCC)(=O)C>[C:13]([CH2:14][CH2:15][O:16][CH2:17][C:18](=[O:38])[CH2:19][C:20]([O:22][CH2:23][CH2:24][CH:25]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:21])([OH:11])=[O:12]

Participants

7

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 24425Chromic AcidHCID 17825661HCID 17825661, compound

Product 1

HCID 17825607HCID 17825607, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

625 mg (6.25 mmol) of chromic acid, 0.65 ml of concentrated sulfuric acid and 2.9 ml of water were added to 1.36 g (3.66 mmol) of 3,3-diphenylpropyl 4-(3-hydroxypropoxy)-3-oxobutanoate in 17 ml of acetone, and they were stirred at room temperature for 1.5 hours. After the addition of water and extraction with ethyl acetate, the organic layer was washed with water and then saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/1) to obtain the title compound.

Workup

  1. washthe organic layer was washed with water
  2. dry with materialsaturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-0360e5a536cd4394be229aca5dc29332
Source dataset
uspto-grants-2007_07
Patent number
US07247645B2

Reaction notes

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