Ethyl formate → 4-methoxy-N-methyl-2-(2-oxo-1-phenylethyl)benzamide

HRID 2196383Notes

Reaction equation

HRID 2196383 reaction equation
[CH2:1]([C:8]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:9]=1[C:10]([NH:12][CH3:13])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[CH:25](OCC)=[O:26]>C1COCC1>[CH3:19][O:18][C:16]1[CH:15]=[CH:14][C:9]([C:10]([NH:12][CH3:13])=[O:11])=[C:8]([CH:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:25]=[O:26])[CH:17]=1

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 225559272-Benzyl-4-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 866102374-methoxy-N-methyl-2-(2-oxo-1-phenylethyl)benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-benzyl-4-methoxy-N-methylbenzamide (125 mg) in 5 mL THF was cooled to −78 C. n-BuLi (0.400 mL, 2.5 M in hexanes) was added, and the reaction was stirred at −78 C for 20 min. A solution of ethyl formate (0.160 mL) in 1 mL THF was added via cannula. The reaction was quenched at −78 C by addition of saturated aqueous ammonium acetate. The mixture was extracted with EtOAc and concentrated to give 4-methoxy-N-methyl-2-(2-oxo-1-phenylethyl)benzamide, which was used without further purification.

Workup

  1. customThe reaction was quenched at −78 C by addition of saturated aqueous ammonium acetate
  2. extractionThe mixture was extracted with EtOAc
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-de7b8ea46bc143fe8a77747a55bdd5c8
Source dataset
uspto-grants-2012_12
Patent number
US08338449B2

Reaction notes

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