Ethyl Acetate → 1-(Thiophen-3-yl)propan-1-one

HRID 626103Notes

Reaction equation

HRID 626103 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]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 22489894N-methoxy-N-methylthiophene-3-carboxamideHCID 178461630HCID 178461630, compound

Product 1

HCID 5299441-(Thiophen-3-yl)propan-1-oneYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. additionOnce the addition
  2. washThe reaction mixture was washed with saturated NH4Cl (aq)
  3. customdried
  4. concentrationconcentrated
  5. 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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