Hydrochloric Acid → 2-Hydroxysorbinil

HRID 482695노트

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HRID 482695 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12]3)[CH2:10][C:9](=[O:18])[O:8][C:5]2=[CH:6][CH:7]=1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>CCCCCC.O1CCCC1>[OH:18][CH:9]1[CH2:10][C:11]2([C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12]2)[C:4]2[C:5](=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[O:8]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 13644525HCID 13644525, 화합물HCID 21225700Diisobutylaluminumhydride2회

생성물 1

HCID 1963682-Hydroxysorbinil

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

To a slurry of 640 mg. (0.002 mole) of 6-fluorospiro[chroman-4,4'-imidazolidine]2,2',5'-trione in 40 ml. of toluene at -78° C. was added 852 mg. (0.006 mole) of diisobutylaluminum hydride in hexane, and the reaction mixture allowed to stir at -78° C. for 30 minutes. The reaction was allowed to warm to 0° C. and was stirred for 24 hours. The reaction was recooled to -40° C., 6 ml. of dry tetrahydrofuran was added and the reaction warmed to 0° C. Additional diisobutylaluminum hydride (1.0 ml) was added in 0.2 ml. portions. The reaction mixture was added to 10% hydrochloric acid and the mixture extracted with ethyl acetate. The combined extracts were washed dried and concentrated to dryness. The residue was chromatographed to give 67 mg. of the desired compound, m.p. 247°-251° C. (dec.).

후처리

  1. temperatureto warm to 0° C.
  2. stirringwas stirred for 24 hours
  3. customwas recooled to -40° C.
  4. temperaturethe reaction warmed to 0° C
  5. extractionthe mixture extracted with ethyl acetate
  6. washThe combined extracts were washed
  7. customdried
  8. concentrationconcentrated to dryness
  9. customThe residue was chromatographed
  10. customto give 67 mg

출처 및 근거

ORD 기록
ord-47492f45226e4e0891b1e34bdb9d9c49
출처 데이터셋
uspto-grants-1986_03
특허 번호
US04575507

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