Isopropenyl acetate → Cholesta-1,5,7-trien-3-ol

HRID 3984

反応式

HRID 3984 の反応式
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH:19]=[CH:20]2)[CH:15]=[CH:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].C(OC(C)=C)(=O)C.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>CO.C(O)C.C(O)(=O)C>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][CH:18]([OH:28])[CH:19]=[CH:20]2)=[CH:15][CH:14]=3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

参加物

8

反応物 4

HCID 7916Isopropenyl acetateHCID 1073901,4,6-Cholestatrien-3-oneHCID 4311764Sodium borohydrideHCID 5284359Calcium Chloride

生成物 1

HCID 18611553Cholesta-1,5,7-trien-3-ol収率 63%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a mixture of 38 g (0.1 mol) of cholesta-1,4,6-trien-3-one and 17 g (0.1 mol) of paratoluenesulfonic acid were added 400 g (4 mol) of isopropenyl acetate, and the mixture was heated under reflux for 3 hours. The reaction solution was thoroughly washed with water until it was neutral, and dried over sodium sulfate A solution of the thus obtained concentrate in 600 ml of ether was added dropwise at a temperature of -5° C. to -10° C. to a reducer solution and stirred at 0° C. for 6 hours, said reducer solution being prepared by cooling a solution of 90 g of calcium chloride in 1,500 ml of methanol to a temperature of -5° C. to -10° C., then adding dropwise thereto a solution of 45 g of sodium borohydride in 2,000 ml of ethanol, and stirring the reaction solution at a temperature of -5° C. to -10° C. for 60 minutes. After completion of the reaction, 50% acetic acid was added to the reaction mixture and the resultant solution was extracted with ether. The ethereal layer separated was washed with water and then sodium bicarbonate solution, dried over sodium sulfate and distilled under reduced pressure to remove ether therefrom. The residue was recrystallized from acetone to yield 23.9 g of cholesta-1,5,7-trien-3-ol (IV), m.p. 126°-127° C. The yield was 63%.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. washThe reaction solution was thoroughly washed with water until it
  4. dry with materialdried over sodium sulfate A solution of the
  5. customthus obtained
  6. concentrationconcentrate in 600 ml of ether
  7. additionwas added dropwise at a temperature of -5° C. to -10° C. to a reducer solution
  8. custombeing prepared
  9. additionadding dropwise
  10. additionwas added to the reaction mixture
  11. extractionthe resultant solution was extracted with ether
  12. customThe ethereal layer separated
  13. washwas washed with water
  14. dry with materialsodium bicarbonate solution, dried over sodium sulfate
  15. distillationdistilled under reduced pressure
  16. customto remove ether
  17. customThe residue was recrystallized from acetone

出典と根拠

ORDレコード
ord-0ef1704cd51e4103bf0c70a5c34931c8
出典データセット
uspto-grants-1988_02
特許番号
US04723045

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