N-Methoxy-N-methylbenzofuran-5-carboxamide → 1-(Benzofuran-5-yl)propan-1-one

HRID 1671315Notes

Reaction equation

HRID 1671315 reaction equation
CON(C)[C:4]([C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]=[CH:11][C:10]=2[CH:14]=1)=[O:5].[CH2:16]([Mg]Br)[CH3:17]>CCOCC>[O:13]1[C:9]2[CH:8]=[CH:7][C:6]([C:4](=[O:5])[CH2:16][CH3:17])=[CH:14][C:10]=2[CH:11]=[CH:12]1

Participants

4

Reactant 2

HCID 59186071N-Methoxy-N-methylbenzofuran-5-carboxamideHCID 178418443HCID 178418443, compound

Product 1

HCID 673362701-(Benzofuran-5-yl)propan-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

An ice-cooled mixture comprising N-methoxy-N-methylbenzofuran-5-carboxamide (1 g, 4.87 mmol) in dry ether (20 ml) under N2 is treated dropwise with ethylmagnesium bromide (2.437 ml, 7.31 mmol). After stirring for 30 mins the mixture is allowed to warm to RT. The reaction is quenched by careful addition of NH4Cl followed by 1M HCl and the contents are transferred to a separating funnel. The mixture is extracted with EtOAc and the organic portion is washed with 1M NaOH, brine, dried (MgSO4), evaporated down to give a light brown oil, which began to crystallise on standing. Purification by chromatography on silica eluting with 25% EtOAc/iso-Hex affords the title compound as a white crystalline solid. 1H NMR (400 MHz, CDCl3) δ 8.2 (d, 1H), 7.9 (d, 1H), 7.6 (d, 1H), 7.45 (d, 1H), 6.8 (d, 1H), 3.0 (q, 2H), 1.2 (t, 3H).

Workup

  1. customThe reaction is quenched by careful addition of NH4Cl
  2. customthe contents are transferred to a separating funnel
  3. extractionThe mixture is extracted with EtOAc
  4. washthe organic portion is washed with 1M NaOH, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated down
  7. customto give a light brown oil, which
  8. customto crystallise
  9. customPurification by chromatography on silica eluting with 25% EtOAc/iso-Hex

Sources & evidence

ORD record
ord-6d250ffdd261496d98dd3b9fcca114dd
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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