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

HRID 414643노트

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HRID 414643 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

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온도
-23 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-152dd11dbeb94ad9b549f774c94fa9c9
출처 데이터셋
uspto-grants-1988_12
특허 번호
US04792614

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