Diethyl Ether → HCID 68884452, compound

HRID 2111016Notes

Reaction equation

HRID 2111016 reaction equation
[OH:1][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][S:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:13][CH:12]=1)[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C([O-])(=O)C.[Na+].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(OCC)C>ClCCl>[CH3:24][O:23][C:21](=[O:22])[CH2:20][CH2:19][S:18][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:2](=[O:1])[CH2:3][C:4]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:5])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 517045Sodium AcetateHCID 2724130Cornforth reagentHCID 68882697HCID 68882697, compound

Product 1

HCID 68884452HCID 68884452, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (15 ml) of tert-butyl 3-hydroxy-3-(4-{[(3-methoxy-3-oxopropyl)thio]methyl}phenyl)propionate (695 mg, 1.96 mmol) in dichloromethane were added sodium acetate (810 mg, 9.87 mmol) and pyridinium dichromate (885 mg, 2.35 mmol), and the mixture was stirred overnight at room temperature. Ethyl ether was added to the reaction mixture, and the mixture was filtered. The filtrate was concentrated under reduced pressure, and the obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate=5:1) to give the title compound (494 mg, 71%).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe obtained crude product
  4. customwas purified by silica gel chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-0f6baec97d8c43c1b9e17a9ae578925b
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

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