Phosphorus oxychloride → 3-(5-Methyl-3-p-fluorophenyl-furan-2-yl)acrylaldehyde

HRID 414643ノート

反応式

HRID 414643 の反応式
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[CH:9][CH:10]=[O:11].[CH3:13][C:14]1[O:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH:18]=1>C(#N)C>[CH3:13][C:14]1[O:15][C:16]([CH:8]=[CH:9][CH:10]=[O:11])=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH:18]=1

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 791253-(Dimethylamino)-2-propenalHCID 144246752-Methyl-4-(4'-fluorophenyl)furan

生成物 1

HCID 542838993-(5-Methyl-3-p-fluorophenyl-furan-2-yl)acrylaldehyde収率 97%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
-23 °C

実験手順

A solution of 1.1 mL (11.9 mmol) of phosphorus oxychloride in 15 mL of acetonitrile was allowed to react with 1.2 mL (11.9 mmol) of 3-dimethylaminoacrolein at -23° C. After 0.25 hour at -23° C., 1.4 g (7.9 mmol) of 2-methyl-4-(4'-fluorophenyl)furan in 10 mL of acetonitrile was added dropwise. The reaction mixture was stirred at -23° C. for 0.15 hour then at 24° C. for 2 hours. The reaction was quenched upon treatment with 20 mL of 1M NaOH and extracted three times with CHCl3. The CHCl3 layers were combined, dried (MgSO4) and concentrated under reduced pressure. Column chromatography (3:1 hexanes-diethyl ether) of the residue on silica gel produced 1.76 g (97%) of 3-(5-methyl-3-p-fluorophenyl-furan-2-yl)acrylaldehyde as a solid (m.p. 89°-90° C.), homogeneous by TLC and spectroscopic criteria; Rf 0.58 (1:1 hexanes-diethyl ether); IR (KBr) 1655, 1600, 1205, 1118, 1095 cm-1 ; 1HNMR (300 MHz, CDCl3) 9.60 (d, 1H, J=10.5 Hz), 7.41 (m, 2H), 7.27 (d, 1H, J=15 Hz), 7.18 (t, 2H, J=9.0 Hz), 6.64 (dd, 1H, J=10.5 Hz, 15 Hz), 6.32 (s, 1H), 2.42 (s, 3H).

後処理

  1. waitat 24° C. for 2 hours
  2. customThe reaction was quenched upon treatment with 20 mL of 1M NaOH
  3. extractionextracted three times with CHCl3
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-152dd11dbeb94ad9b549f774c94fa9c9
出典データセット
uspto-grants-1988_12
特許番号
US04792614

反応ノート

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