3-Bromofuran → HCID 19047515、化合物

HRID 742480ノート

反応式

HRID 742480 の反応式
C([Li])CCC.Br[C:7]1[CH:11]=[CH:10][O:9][CH:8]=1.CN(OC)[C:14]([C:16]1[CH:20]=[CH:19][O:18][CH:17]=1)=[O:15]>CCOCC>[O:9]1[CH:10]=[CH:11][C:7]([C:14]([C:16]2[CH:20]=[CH:19][O:18][CH:17]=2)=[O:15])=[CH:8]1

参加物

5

反応物 3

HCID 891643-BromofuranHCID 10487090N-methoxy-N-methylfuran-3-carboxamideHCID 178418339Butyllithium

生成物 1

HCID 19047515HCID 19047515、化合物収率 78.4%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒3 回

反応条件

温度
-78 °C

実験手順

To a solution of n-butyllithium (2.5M, 28 mL, 0.07 mol) in 150 mL of ether at -78 ° C. was added a solution of 3-bromofuran (10 g, 0.0628 mol) in 30 mL of ether over a 20 min period and the mixture was stirred at -78° C. for 20 min. To the above mixture was added 3-(N-methyl-N-methoxycarbamoyl)furan (9.16 g, 0.059 mol) in 30 mL of ether over a 15 min period and the mixture was stirred at room temperature for 1/2 h. The reaction mixture was quenched with 200 mL of ammonium chloride solution, 500 mL of methylene chloride was added and the mixture was stirred. The organic layer was dried over sodium sulfate, concentrated in vacuo, and the residue was triturated with 100 mL of hexane/TBME (9:1). The solid product was filtered and washed with TBME to afford 7.5 g (78.3%) of di-(3-furyl)ketone.

後処理

  1. stirringthe mixture was stirred at room temperature for 1/2 h
  2. customThe reaction mixture was quenched with 200 mL of ammonium chloride solution, 500 mL of methylene chloride
  3. additionwas added
  4. stirringthe mixture was stirred
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customthe residue was triturated with 100 mL of hexane/TBME (9:1)
  8. filtrationThe solid product was filtered
  9. washwashed with TBME

出典と根拠

ORDレコード
ord-c5a84b13b2a0486083e61ac834e25af2
出典データセット
uspto-grants-1996_09
特許番号
US05554620

反応ノート

読み込み中…