(Diethylamino)sulfur trifluoride → 2-Fluoromethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one

HRID 1900720

반응식

HRID 1900720 반응식
O[CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3.C(N(S(F)(F)[F:24])CC)C>C(Cl)Cl>[F:24][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3

참가 물질

4

반응물 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 233696792-Hydroxymethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

생성물 1

HCID 233697882-Fluoromethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one수율 32.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

2-Hydroxymethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (500 mg) was suspended in anhydrous methylene chloride (20 ml). To the suspension, diethylaminosulfur trifluoride (DAST) (372 mg) was added while stirring and cooling at -78° C. Subsequently, the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, methylene chloride was further added thereto, and washed with aqueous sodium bicarbonate solution, and aqueous NaCl solution in this order. After drying, the solvent was distilled off to obtain 487 mg of a crude product. The crude product was purified by silica gel column chromatography (eluent=chloroform:methanol=400:1-20:1), and then by separative thin layer chromatography (developer=chloroform:methanol=10:1) to obtain a purified product, which was subjected to recrystallization using a solvent mixture of chloroform and n-hexane to obtain 163 mg of colorless needles (32%).

후처리

  1. stirringSubsequently, the mixture was stirred at room temperature for 30 minutes
  2. additionwas further added
  3. washwashed with aqueous sodium bicarbonate solution, and aqueous NaCl solution in this order
  4. customAfter drying
  5. distillationthe solvent was distilled off
  6. customto obtain 487 mg of a crude product
  7. customThe crude product was purified by silica gel column chromatography (eluent=chloroform:methanol=400:1-20:1)
  8. customby separative thin layer chromatography (developer=chloroform:methanol=10:1) to obtain a purified product, which
  9. customwas subjected to recrystallization
  10. additiona solvent mixture of chloroform and n-hexane

출처 및 근거

ORD 기록
ord-85f2a33677444530885fd7203c576ab0
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05576324

연결된 노트

불러오는 중…