N-(2-Chloro-6-(hydroxymethyl)phenyl)pivalamide → N-(5-Chloro-2-formylphenyl)-2,2-dimethylpropionamide

HRID 132249Notes

Reaction equation

HRID 132249 reaction equation
[Cr]([Cl:5])([O-])(=O)=O.[NH+]1C=CC=CC=1.Cl[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][OH:20])[C:14]=1[NH:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[Cl:5][C:18]1[CH:17]=[CH:16][C:15]([CH:19]=[O:20])=[C:14]([NH:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH:13]=1

Participants

4

Reactant 2

HCID 67318310N-(2-Chloro-6-(hydroxymethyl)phenyl)pivalamideHCID 178418287HCID 178418287, compound

Product 1

HCID 57431473N-(5-Chloro-2-formylphenyl)-2,2-dimethylpropionamideYield 47.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium chlorochromate (1.19 g, 5.5 mmol) was added to a solution of N-(2-chloro-6-(hydroxymethyl) phenyl) pivalamide (884 mg, 3.67 mmol) in CH2Cl2 (100 mL) at 0° C. 5 min later the mixture was allowed stirring at room temperature for 3 hrs. The reaction mixture was passed through a thin pad layer of silica gel with CH2Cl2 (2×100 mL), concentrated on rotary vacuo, and purified on a flash chromatography column eluting with 20˜50% EtOAc/hexanes (1000 mL) to afford the expected product as a white solid (414 mg, 47% yield); 1H NMR (400 MHz, CDCl3) δ ppm 1.37 (s, 9 H), 7.30 (t, J=7.81 Hz, 1H), 7.64 (dd, J=7.93, 1.39 Hz, 1 H), 7.77 (dd, J=7.55, 1.51 Hz, 1 H), 8.25 (s, 1 H), 9.84 (s, 1 H); Mass spec. 240.08 (MH+), Calc. for C12H14ClNO2 239.07.

Workup

  1. concentrationconcentrated on rotary vacuo
  2. custompurified on a flash chromatography column
  3. washeluting with 20˜50% EtOAc/hexanes (1000 mL)

Sources & evidence

ORD record
ord-3b8902cf92934c69967c8726498d7002
Source dataset
uspto-grants-2008_06
Patent number
US07384930B2

Reaction notes

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