Ethanol → Colestolone

HRID 1721306ノート

反応式

HRID 1721306 の反応式
C([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH:14]=[C:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C@@:16]43[O:37][C@H:17]4[CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11]1)(=O)C1C=CC=CC=1.C(O)C.S(=O)(=O)(O)O>O>[OH:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C:16]=3[C:17](=[O:37])[CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11]1

参加物

5

反応物 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14696446HCID 14696446、化合物

生成物 1

HCID 10046567Colestolone収率 146.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
5 °C

実験手順

A mixture of 3β-benzoyloxy-14α,15α-epoxy-5α-cholest-7-ene (26, 12.0 g, 23.8 mmol), 95% ethanol (300 mL), and water (35 mL) was cooled to 5° C. in an ice water bath. To this solution was added, in portions of 5 mL, concentrated sulfuric acid (65.0 mL). After the addition (~5 min) the reaction mixture was heated under reflux for 22 h. Stirring must be effective to prevent clumping of the starting material. The clear reaction mixture was cooled to ambient temperature, then poured into ice (700 g). A sticky precipitate was formed (could not be filtered). The water phase was extracted three times with ethyl acetate (400, 200, and 200 mL). The combined ethyl acetate phase was washed with water, 5% sodium bicarbonate, and sodium chloride solution, and dried over sodium sulfate. Evaporation of the solvent gave a semisolid yellowish compound (14 g). The crude compound 27 was purified by flash chromatography (4.0×35 cm column) and eluted with ethyl acetate/hexane (1:3). Fractions containing product were combined and evaporated to give after crystallization from methanol/water pure product as fine needles 4.5 (47%). Mp, NMR, and IR data were in agreement with published data.

後処理

  1. additionAfter the addition (~5 min) the reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 22 h
  4. temperatureThe clear reaction mixture was cooled to ambient temperature
  5. customA sticky precipitate was formed (could not
  6. filtrationbe filtered)
  7. extractionThe water phase was extracted three times with ethyl acetate (400, 200, and 200 mL)
  8. washThe combined ethyl acetate phase was washed with water, 5% sodium bicarbonate, and sodium chloride solution
  9. dry with materialdried over sodium sulfate
  10. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-54a10f52bed14da0ba3c16966ca3dd66
出典データセット
uspto-grants-1996_04
特許番号
US05510340

反応ノート

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