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

HRID 559668Notes

Reaction equation

HRID 559668 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-b2073fade71b4f3b82eda67b80d7bdbc
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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