Pyridine → 6alpha,7alpha-Diepoxypregn-4-en-3beta-yl acetate

HRID 1196317ノート

反応式

HRID 1196317 の反応式
[O:1]1[C:19]2=[C:20]3[C@:15]([CH3:22])([CH2:16][CH2:17][C@@H:18]2[OH:21])[C@@H:14]2[C@H:4]([C@H:5]4[C@:11]([CH3:23])([CH2:12][CH2:13]2)[C@@H:8]([CH2:9][CH3:10])[CH2:7][CH2:6]4)[C@@H:3]2[O:24][C@:2]123.N1C=CC=CC=1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>C(Cl)Cl>[C:31]([O:21][C@H:18]1[CH2:17][CH2:16][C@@:15]2([CH3:22])[C:20]3[C@:2]4([O:1][C:19]1=3)[O:24][C@H:3]4[C@@H:4]1[C@@H:14]2[CH2:13][CH2:12][C@@:11]2([CH3:23])[C@H:5]1[CH2:6][CH2:7][C@@H:8]2[CH2:9][CH3:10])(=[O:33])[CH3:32]

参加物

5

反応物 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 867457996alpha,7alpha-Diepoxypregn-4-en-3beta-ol

生成物 1

HCID 867458006alpha,7alpha-Diepoxypregn-4-en-3beta-yl acetate収率 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a mixture of 0.084 g (0.189 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α;6α,7α-diepoxypregn-4-en-3β-ol, 0.5 ml (6.18 mmoles) of dry pyridine and 5 ml of methylene chloride was gradually added 0.1 ml (1.06 mmoles) of acetic anhydride dropwise at a temperature of 0° C. and the solution was stirred at room temperature for 8 hours. The reaction mixture thus obtained was diluted with methylene chloride and washed with saturated aqueous copper (II) sulfate solution. The aqueous layer (washings) was extracted with methylene chloride and the extract was combined with the organic layer. The resulting mixture was washed with water and aqueous sodium chloride solution in that order and dired over magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane: 1:10, v/v) to recover 0.083 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α;6α,7α-diepoxypregn-4-en-3β-yl acetate (yield: 90%).

後処理

  1. additionTo a mixture of 0.084 g (0.189 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α
  2. customdropwise at a temperature of 0° C.
  3. customThe reaction mixture thus obtained
  4. washwashed with saturated aqueous copper (II) sulfate solution
  5. extractionThe aqueous layer (washings) was extracted with methylene chloride
  6. washThe resulting mixture was washed with water and aqueous sodium chloride solution in that order
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customthe residue was purified by silica gel chromatography (eluent
  9. customethyl acetate-hexane: 1:10, v/v) to recover 0.083 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α

出典と根拠

ORDレコード
ord-f5fcedadc12a445fb90b776e58929db0
出典データセット
uspto-grants-1992_05
特許番号
US05112998

反応ノート

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