N-Methoxy-N-methyl-2-(2-methylphenyl)acetamide → 1-(2-Methylphenyl)but-3-en-2-one

HRID 1644774Notes

Reaction equation

HRID 1644774 reaction equation
[CH:1]([Mg]Br)=[CH2:2].CON(C)[C:8](=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16]>C1COCC1.CCOCC>[CH3:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][C:8](=[O:17])[CH:1]=[CH2:2]

Participants

5

Reactant 2

HCID 21099310N-Methoxy-N-methyl-2-(2-methylphenyl)acetamideHCID 178418507HCID 178418507, compound

Product 1

HCID 210992901-(2-Methylphenyl)but-3-en-2-oneYield 83.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of vinylmagnesium bromide (220 mL, 1.0 M, 220 mmol) in 100 mL THF, was added dropwise under nitrogen atmosphere at 0° C. a solution of 2-(2-methylphenyl)-N-methoxy-N-methylacetamide (Step A, 21 g, 106.6 mmol) in ˜150 mL dry ether. The reaction mixture was stirred at 0° C. for 0.5 hr then poured slowly into an ice/2N aq HCl (300 mL) mixture. The resulting mixture was diluted with ether, transferred to a separation funnel. The organic layer was separated, washed with brine, dried over MgSO4, filtered and the solvent evaporated under vacuum to give 14.2 g of the crude title compound which was used without further purification. 1H-NMR (CDCl3): δ: 7.15-7.25 (4H, m), 6.47 (1H, dd, J1=14.2 Hz, J2=11 Hz), 6.35 (1H, d, J=14.2 Hz), 5.86 (1H, d, J=11 Hz), 3.83 (2H, s), 2.28 (3H, s).

Workup

  1. customtransferred to a separation funnel
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-a7ceeb9ad9a2481ab3c6148bb7524d13
Source dataset
uspto-grants-2012_02
Patent number
US08124633B2

Reaction notes

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