Hydrochloric Acid → 2-Hydroxysorbinil

HRID 482695ノート

反応式

HRID 482695 の反応式
[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

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 13644525HCID 13644525、化合物HCID 21225700Diisobutylaluminumhydride2 回

生成物 1

HCID 1963682-Hydroxysorbinil

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-47492f45226e4e0891b1e34bdb9d9c49
出典データセット
uspto-grants-1986_03
特許番号
US04575507

反応ノート

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