Ethyl Acetate → HCID 13186545, compound

HRID 924945Notes

Reaction equation

HRID 924945 reaction equation
CON(C)[C:4]([C:6]1[CH:10]=[CH:9][O:8][CH:7]=1)=[O:5].[CH2:12]([Mg]Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCOC(C)=O.[NH4+].[Cl-]>C1COCC1>[O:8]1[CH:9]=[CH:10][C:6]([C:4](=[O:5])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 10487090HCID 10487090, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 13186545HCID 13186545, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-methoxy-N-methylfuran-3-carboxamide (913 mg, 5.89 mmol) in anhydrous THF (10 mL) was cooled to −78° C. under nitrogen, and a solution of benzylmagnesium chloride in THF (2 mol/L, 3.53 mL) was added through a syringe. The reaction mixture was stirred at this temperature for 5 hours. TLC (PE:EtOAc=5:1) indicated reaction was nearly complete, saturated NH4Cl solution (20 mL) was added to quench the reaction, and the aqueous layer was extracted with EtOAc (80 mL). The organic layer was washed with brine (30 mL), dried over Na2SO4, filtered, and concentrated to afford 1-(furan-3-yl)-2-phenylethanone as a yellow oil (696 mg, yield: 63.2%).

Workup

  1. customreaction
  2. customto quench
  3. customthe reaction
  4. extractionthe aqueous layer was extracted with EtOAc (80 mL)
  5. washThe organic layer was washed with brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2af9adb1692a45f592c54689f9c8b6c7
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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