N-(3-fluoro-2-(hydroxymethyl)phenyl)pivalamide → N-(3-fluoro-2-formylphenyl)pivalamide

HRID 132389Notes

Reaction equation

HRID 132389 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[F:12][C:13]1[C:14]([CH2:26][OH:27])=[C:15]([NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH:16]=[CH:17][CH:18]=1>C(Cl)Cl>[F:12][C:13]1[C:14]([CH:26]=[O:27])=[C:15]([NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:22])[CH3:23])[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 59732042N-(3-fluoro-2-(hydroxymethyl)phenyl)pivalamideHCID 178418287HCID 178418287, compound

Product 1

HCID 59731973N-(3-fluoro-2-formylphenyl)pivalamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium chlorochromate (596 mg, 2.76 mmol) was added to a solution of N-(3-fluoro-2-(hydroxymethyl) phenyl)pivalamide (415 mg, 1.84 mmol) in CH2Cl2 (50 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(2×50 mL), concentrated on rotary vacuum, and purified on a flash chromatography column eluting with 20˜50% EtOAc/hexanes (600 mL) to afford the expected product, N-(3-fluoro-2-formylphenyl)pivalamide, as a white solid (396 mg, 46% yield after five steps); 1H NMR (400 MHz, CDCl3) δ ppm 1.33 (s, 9 H), 6.76-6.83 (m, 1 H), 7.54 (td, J=8.44, 6.55 Hz, 1 H), 8.56 (d, J=8.56 Hz, 1 H), 10.38 (s, 1 H), 11.57 (s, 1 H); Mass spec. 224.11 (MH+), Calc. for C12H14FNO2 223.1.

Workup

  1. concentrationconcentrated on rotary vacuum
  2. custompurified on a flash chromatography column
  3. washeluting with 20˜50% EtOAc/hexanes (600 mL)

Sources & evidence

ORD record
ord-ad14ca1cc700404ca2874b50db612f11
Source dataset
uspto-grants-2008_06
Patent number
US07384931B2

Reaction notes

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