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

HRID 83861Notes

Reaction equation

HRID 83861 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-d79a84b0c63641a6b23db223460aa37a
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

Loading…