Tetrahydrofuran → 1-methyl-4-propionylpyridin-2(1H)-one

HRID 626188Notes

Reaction equation

HRID 626188 reaction equation
CON(C)[C:4]([C:6]1[CH:11]=[CH:10][N:9]([CH3:12])[C:8](=[O:13])[CH:7]=1)=[O:5].[CH2:15]1COC[CH2:16]1>>[CH3:12][N:9]1[CH:10]=[CH:11][C:6]([C:4](=[O:5])[CH2:15][CH3:16])=[CH:7][C:8]1=[O:13]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 60731291N-methoxy-N,1-dimethyl-2-oxo-1,2-dihydropyridine-4-carboxamide

Product 1

HCID 896573541-methyl-4-propionylpyridin-2(1H)-oneYield 62%

Procedure

To a solution of N-methoxy-N,1-dimethyl-2-oxo-1,2-dihydropyridine-4-carboxamide (200 mg, 1.0 eq) in 10 mL anhydrous THF was added 3 M EtBrMg (0.7 mL, 2 eq) slowly at 0° C. The reaction was stirred at rt for 1 h., quenched with sat NH4Cl (aq), and extracted with CH2Cl2. The extract was dried, concentrated, and purified by column chromatography to give the desired product (105 mg, 62% yield). 1H NMR (400 MHz, CDCl3) δ 7.35 (d, J=6.8 Hz, 1H), 7.06 (d, J=2.0 Hz, 1H), 6.61 (dd, J=6.8 Hz, 1.6 Hz, 1H), 3.57 (s, 3H), 2.89 (q, J=7.2 Hz, 2H), 1.20 (t, J=7.2 Hz, 3H).

Workup

  1. customquenched with sat NH4Cl (aq)
  2. extractionextracted with CH2Cl2
  3. customThe extract was dried
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-8a7ac739a9e245f0bfba5a58ccff63d9
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

Loading…