Hydrochloric Acid → 1-(3-Furanyl)-1-propanone

HRID 1451340Notes

Reaction equation

HRID 1451340 reaction equation
CN(OC)[C:3]([C:5]1[CH:9]=[CH:8][O:7][CH:6]=1)=[O:4].C[Mg]Br.Cl.[CH2:16]1COC[CH2:17]1>CCOCC>[O:7]1[CH:8]=[CH:9][C:5]([C:3](=[O:4])[CH2:16][CH3:17])=[CH:6]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 10487090HCID 10487090, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 150538531-(3-Furanyl)-1-propanoneYield 70.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-(N-methyl-N-methoxycarbamoyl)furan (14 g, 0.09 mol) in 150 ml of THF cooled to -78° C. was added in portions 36.1 ml (0.108 mol) of 3M methylmagnesium bromide in ether and the mixture was allowed to warm to room temperature, and then stirred for 30 min. To the above mixture was added a cold 2N HCl (100 ml) and the aqueous layer was extracted with ether (3×100 ml), the combined organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo to yield a pale-yellow oil. The above oil was chromatographed on silica (methylene chloride/hexane 2:1) to afford 6.95 g (70.2%) of 1-(3-furyl)-1-propanone as a colorless oil which crystallized as a white solid.

Workup

  1. extractionthe aqueous layer was extracted with ether (3×100 ml)
  2. washthe combined organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto yield a pale-yellow oil
  6. customThe above oil was chromatographed on silica (methylene chloride/hexane 2:1)

Sources & evidence

ORD record
ord-42bc2e4f9ea8492986c2ec02197f55d9
Source dataset
uspto-grants-1997_02
Patent number
US05604224

Reaction notes

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