2-(4-fluoro-3-methoxyphenyl)-N-methoxy-N,2-dimethylpropanamide → HCID 66740026, compound

HRID 1627346Notes

Reaction equation

HRID 1627346 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:16])([CH3:15])[C:9](N(OC)C)=[O:10])=[CH:4][C:3]=1[O:17][CH3:18].[Li][CH3:20]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:15])([CH3:16])[C:9](=[O:10])[CH3:20])=[CH:4][C:3]=1[O:17][CH3:18]

Participants

4

Reactant 2

HCID 866622452-(4-fluoro-3-methoxyphenyl)-N-methoxy-N,2-dimethylpropanamideHCID 178418348HCID 178418348, compound

Product 1

HCID 66740026HCID 66740026, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-fluoro-3-methoxyphenyl)-N-methoxy-N,2-dimethylpropanamide (123 g, 0.48 mol) in THF (1 L)-78° C. was added 3M ethereal solution of MeLi (210 mL, 0.627 mol). The resulting solution was warmed to ambient temperature and stirred 16 h. The reaction mixture was quenched with 3N HCl (400 mL) and extracted with EtOAc (600 mL×2). The combined extracts were washed with satd NaHCO3 (1.0 L) and brine (1.0 L), then dried over MgSO4 and concentrated at reduced pressure to give 3-(4-fluoro-3-methoxyphenyl)-3-methylbutan-2-one as yellow color oil (92.5 g, 91%). 1H NMR (400 MHz, CDCl3): δ 7.05 (m, 1H), 6.83-6.78 (m, 2H), 3.88 (s, 3H), 1.95 (s, 3H), 1.47 (s, 6H).

Workup

  1. customThe reaction mixture was quenched with 3N HCl (400 mL)
  2. extractionextracted with EtOAc (600 mL×2)
  3. washThe combined extracts were washed with satd NaHCO3 (1.0 L) and brine (1.0 L)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-9de12db31b30483d97ee0809f70d8934
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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