HCID 131724336, compound → HCID 12973097, compound

HRID 2119983Notes

Reaction equation

HRID 2119983 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][CH:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])[O:8][Si](C)(C)C)[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][C:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])=[O:8])[CH3:2]

Participants

4

Reactant 2

HCID 131724336HCID 131724336, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 12973097HCID 12973097, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-nitro-phenyl)-4-trimethlysilanyloxy-butyric acid ethyl ester (530 mg, 1.6 mmol) in dry DCM (5 mL) under Argon was added PCC (pyridinium chlorochromate) (878 mg, 4.1 mmol) and the resulting mixture stirred vigorously for 20 h. Then silica gel (5 g) was added and the mixture filtered. The filtrate was then evaporated and the residue purified by chromatography on silica gel, eluting with ethyl acetate: hexane (3:1) to afford the title compound (375 mg, 92%) as a colorless liquid; m/z 252 (MH).

Workup

  1. additionThen silica gel (5 g) was added
  2. filtrationthe mixture filtered
  3. customThe filtrate was then evaporated
  4. customthe residue purified by chromatography on silica gel
  5. washeluting with ethyl acetate: hexane (3:1)

Sources & evidence

ORD record
ord-31b0573a546347f99f3f9c517699c154
Source dataset
uspto-grants-2004_02
Patent number
US06686352B2

Reaction notes

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