N-(5-Chloro-2-(hydroxymethyl)phenyl)pivalamide → N-(5-Chloro-2-formylphenyl)-2,2-dimethylpropionamide

HRID 132377Notes

Reaction equation

HRID 132377 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:26][OH:27])=[C:17]([NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=1>C(Cl)Cl>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([CH:26]=[O:27])=[C:17]([NH:19][C:20](=[O:25])[C:21]([CH3:22])([CH3:23])[CH3:24])[CH:18]=1

Participants

4

Reactant 2

HCID 57431472N-(5-Chloro-2-(hydroxymethyl)phenyl)pivalamideHCID 178418287HCID 178418287, compound

Product 1

HCID 57431473N-(5-Chloro-2-formylphenyl)-2,2-dimethylpropionamideYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridiniumchlorochromate (1.67 g, 7.77 mmol) was added to N-(5-chloro-2-(hydroxymethyl)phenyl)pivalamide (1.34 g, 5.55 mmol) in CH2Cl2 (100 mL) at 0° C. 5 min later, the reaction mixture was stirred at room temperature for 3 hrs. Then it was passed through a thin silica gel pad with CH2Cl2 (100 mL), concentrated on rotary vacuum and purified on flash chromatography eluting with 20˜40% EtOAc/hexanes (800 mL) to afford the expected product as a white solid (937 mg, 70% yield). 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.28-1.34 (s, 9 H), 7.15 (dd, J=8.31, 2.01 Hz, 1 H), 7.53-7.59 (m, 1 H), 8.87 (d, J=2.01 Hz, 1 H), 9.84-9.88 (m, 1 H), 11.42 (s, 1 H); Mass spec. 240.07 (MH+), Calc. for C12H14ClNO2 239.07.

Workup

  1. concentrationconcentrated on rotary vacuum
  2. custompurified on flash chromatography
  3. washeluting with 20˜40% EtOAc/hexanes (800 mL)

Sources & evidence

ORD record
ord-34c7364bce49465faf1a4f5110846e15
Source dataset
uspto-grants-2008_06
Patent number
US07384931B2

Reaction notes

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