Tetrahydrofuran → HCID 67026938, compound

HRID 1908861Notes

Reaction equation

HRID 1908861 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]([CH:14]=[C:15]([CH3:17])[N:16]=1)[C:8](N(OC)C)=[O:9])[CH:2]([CH3:4])[CH3:3].[CH2:18]1COCC1>C[Mg]Br.CCOCC>[CH2:1]([C:5]1[CH:6]=[C:7]([C:8](=[O:9])[CH3:18])[CH:14]=[C:15]([CH3:17])[N:16]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 86639885HCID 86639885, compound

Product 1

HCID 67026938HCID 67026938, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 178418573HCID 178418573, compoundSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 2-isobutyl-N-methoxy-6,N-dimethyl-isonicotinamide (410 mg, 1.74 mmol) in THF (10 mL), methyl magnesium bromide (1.17 mL of a 3 M solution in ether, 3.47 mmol) is added at 5° C. The mixture is stirred at 5° C. for 1.5 h. The reaction is quenched by adding NH4Cl. The mixture is diluted with EA (50 mL), washed with sat. aq. NaHCO3, dried over Na2SO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 1-(2-isobutyl-6-methyl-pyridin-4-yl)-ethanone (280 mg) as a colourless oil. LC-MS: tR=0.84 min; 1H NMR (CDCl3): δ 0.96 (d, J=6.5 Hz, 6H), 2.08-2.20 (m, 1H), 2.62 (s, 3H), 2.65 (s, 3H), 2.74 (d, J=7.3 Hz, 2H), 7.37 (s, 1H), 7.42 (s, 1H).

Workup

  1. customThe reaction is quenched
  2. additionby adding NH4Cl
  3. additionThe mixture is diluted with EA (50 mL)
  4. washwashed with sat. aq. NaHCO3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified by CC on silica gel eluting with heptane:EA 4:1

Sources & evidence

ORD record
ord-685b1390a7a946b3b2536f0e8e97b119
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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