Tetrahydrofuran → HCID 67026938, compound

HRID 2040828Notes

Reaction equation

HRID 2040828 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.

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-0ac764d8b2d345718bef760c2e4868b7
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

Loading…