Ethyl Acetate → HCID 13186545、化合物

HRID 401156ノート

反応式

HRID 401156 の反応式
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

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 10487090N-methoxy-N-methylfuran-3-carboxamideHCID 178418336HCID 178418336、化合物

生成物 1

HCID 13186545HCID 13186545、化合物収率 63.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-d06d39448bbe4d7396814ab9d8788a93
出典データセット
uspto-grants-2014_06
特許番号
US08741915B2

反応ノート

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