Cyclohexanone → HCID 90474078, 화합물

HRID 358132

반응식

HRID 358132 반응식
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O=[CH:9][C@H:10]([C@H:12]([C@@H:14]([C@@H:16]([CH2:18][OH:19])[OH:17])[OH:15])[OH:13])[OH:11].I>ClCCl>[CH2:4]1[CH2:5][CH2:6][C:1]2([O:11][C@@H:10]([C@H:12]3[O:13][C@@H:18]4[O:19][C:1]5([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)[O:17][C@H:16]4[C@H:14]3[OH:15])[CH2:9][O:7]2)[CH2:2][CH2:3]1

참가 물질

5

반응물 3

HCID 7967CyclohexanoneHCID 24841Hydrogen iodideHCID 161658Demannose

생성물 1

HCID 90474078HCID 90474078, 화합물수율 82.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
65 °C

실험 절차

To a mixture of 150 ml of cyclohexanone and 120 ml of dichloromethane were added 10.0 g of D-mannose and 175 mg of hydriodic acid (57%) and the mixture was refluxed with stirring in a water bath at 65° C. for 8 hours. During this reaction, the refluxing solvent was dried with 20 g of Molecular Sieves 3A interposed between the reaction vessel and the cooling jacket. The reaction mixture was diluted with benzene, washed with aqueous sodium bicarbonate and water and dried over anhydrous magnesium sulfate. The solvent and cyclohexanone were distilled off under reduced pressure to give 11.9 g (82.6%) of 2,3:5,6-di-O-cyclohexylidene-α-D-mannofuranose. After recrystallization from cyclohexane, it melted at 122°-124° C.

후처리

  1. temperaturethe mixture was refluxed
  2. customDuring this reaction
  3. dry with materialthe refluxing solvent was dried with 20 g of Molecular Sieves 3A
  4. additionThe reaction mixture was diluted with benzene
  5. washwashed with aqueous sodium bicarbonate and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent and cyclohexanone were distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-9298289001374aa3a10a92d9fc57faa9
출처 데이터셋
uspto-grants-1984_08
특허 번호
US04464530

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