Ethyl Acetate → 1-(Thiophen-3-yl)propan-1-one
Reaction equation
[CH3:1][CH2:2][Mg+].[Br-].CON(C)[C:8]([C:10]1[CH:14]=[CH:13][S:12][CH:11]=1)=[O:9].CCOC(C)=O>C1COCC1>[S:12]1[CH:13]=[CH:14][C:10]([C:8](=[O:9])[CH2:2][CH3:1])=[CH:11]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
EtMgBr (3 M, 1.2 eq, 18.6 mL) was added to a solution of N-methoxy-N-methylthiophene-3-carboxamide (8 g, 1.0 eq) in dry THF. Once the addition was complete, the mixture was stirred at rt overnight. The reaction mixture was washed with saturated NH4Cl (aq), dried, concentrated, and purified by column chromatography with petroleum ether:EtOAc=5:1 to give the desired product as a yellow oil (3.4 g, 52% yield). 1H NMR (400 MHz, CDCl3) δ 8.05 (s, 1H), 7.56 (d, J=8.0 Hz, 1H), 7.31 (d, J=8.4 Hz, 1H), 2.92 (q, J=7.6 Hz, 2H), 1.21 (t, J=7.6 Hz, 3H).
Workup
- additionOnce the addition
- washThe reaction mixture was washed with saturated NH4Cl (aq)
- customdried
- concentrationconcentrated
- custompurified by column chromatography with petroleum ether
Sources & evidence
- ORD record
- ord-43090a8cc37449a0bc3e5de11753c8f1
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309211B2
Reaction notes
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