Acetic Anhydride → HCID 86735582、化合物

HRID 1679765ノート

反応式

HRID 1679765 の反応式
[C:1]([C@:3]1([OH:23])[CH:9]=[CH:8][C@H:7]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH2:5][CH3:6])[C@@H:18]1[C:13](=[CH:14][C:15](=[O:22])[CH2:16][CH2:17]1)[CH2:12][CH2:11]3)#[CH:2].N1C(C)=CC(C)=CC=1C.[C:33](OC(=O)C)(=[O:35])[CH3:34]>>[C:33]([O:23][C@@:3]1([C:1]#[CH:2])[CH:9]=[CH:8][C@H:7]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH2:5][CH3:6])[C@@H:18]1[C:13](=[CH:14][C:15](=[O:22])[CH2:16][CH2:17]1)[CH2:12][CH2:11]3)(=[O:35])[CH3:34]

参加物

4

反応物 3

HCID 7918Acetic AnhydrideHCID 79532,4,6-TrimethylpyridineHCID 3033968Gestodene

生成物 1

HCID 86735582HCID 86735582、化合物

実験手順

A solution of 2.0 g. of 17α-ethynyl-17β-hydroxy-18-methyl-4,15-estradien-3-one in 40 ml. of collidine and 13 ml. of acetic anhydride is heated to boiling for 5 hours under nitrogen. After cooling, the solution is poured into ice/water. The reaction product is extracted with methylene chloride, washed in succession with 2N hydrochloric acid, sodium bicarbonate solution, and water, and dried over sodium sulfate. The crude product is chromatographed on silica gel. With 25-30% ethyl acetate-hexane, 950 mg. of 17β-acetoxy-17β-ethynyl-18-methyl-4,15-estradien-3-one is eluted which melts, after recrystallization from acetone/methanol, at 163°-164°.

後処理

  1. temperatureAfter cooling
  2. extractionThe reaction product is extracted with methylene chloride
  3. washwashed in succession with 2N hydrochloric acid, sodium bicarbonate solution, and water
  4. dry with materialdried over sodium sulfate
  5. customThe crude product is chromatographed on silica gel
  6. washof 17β-acetoxy-17β-ethynyl-18-methyl-4,15-estradien-3-one is eluted which melts
  7. customafter recrystallization from acetone/methanol
  8. customat 163°-164°

出典と根拠

ORDレコード
ord-824d0cebcb304607832bf4a7b12339c8
出典データセット
uspto-grants-1978_03
特許番号
US04081537

反応ノート

読み込み中…