5-Methanesulfonyl-furan-2-carboxylic acid methoxy-methyl-amide → 1-(5-Methanesulfonyl-furan-2-yl)-propan-1-one

HRID 1698167Notes

Reaction equation

HRID 1698167 reaction equation
CON(C)[C:4]([C:6]1[O:7][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:9][CH:10]=1)=[O:5].[CH2:16]([Mg]Cl)[CH3:17]>C1COCC1>[CH3:14][S:11]([C:8]1[O:7][C:6]([C:4](=[O:5])[CH2:16][CH3:17])=[CH:10][CH:9]=1)(=[O:12])=[O:13]

Participants

4

Reactant 2

HCID 592784855-Methanesulfonyl-furan-2-carboxylic acid methoxy-methyl-amideHCID 178461633HCID 178461633, compound

Product 1

HCID 592781411-(5-Methanesulfonyl-furan-2-yl)-propan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a chilled (0° C.) solution of 5-methanesulfonyl-furan-2-carboxylic acid methoxy-methyl-amide (1.48 g, 6.36 mmol) in THF (30 mL) was added a 2 M solution of ethylmagnesium chloride in THF (7.0 mL, 14 mmol). The mixture was then slowly warmed to with stifling. After 18 hours, the mixture was quenched with saturated aqueous ammonium chloride (50 mL) and then diluted with ethyl acetate (50 mL). The aqueous phase was separated and extracted with ethyl acetate (3×30 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to afford 1-(5-methanesulfonyl-furan-2-yl)-propan-1-one.

Workup

  1. temperatureThe mixture was then slowly warmed to with stifling
  2. customthe mixture was quenched with saturated aqueous ammonium chloride (50 mL)
  3. additiondiluted with ethyl acetate (50 mL)
  4. customThe aqueous phase was separated
  5. extractionextracted with ethyl acetate (3×30 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-69fcef26be8543f0bf38e6e7f9ab6272
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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