Estradiol → beta-Estradiol diacetate

HRID 1357473

反応式

HRID 1357473 の反応式
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][C@@:9]12[C@@H:25]([OH:26])[CH2:24][CH2:23][C@H:22]1[C@H:21]1[C@@H:12]([C:13]3[CH:14]=[CH:15][C:16]([OH:27])=[CH:17][C:18]=3[CH2:19][CH2:20]1)[CH2:11][CH2:10]2.[CH3:28][C:29](C)=[O:30].C(Cl)Cl>N1C=CC=CC=1>[CH3:2][C:1]([O:26][CH:25]1[C:9]2([CH3:8])[CH2:10][CH2:11][CH:12]3[C:13]4[CH:14]=[CH:15][C:16]([O:27][C:29]([CH3:28])=[O:30])=[CH:17][C:18]=4[CH2:19][CH2:20][CH:21]3[CH:22]2[CH2:23][CH2:24]1)=[O:3]

参加物

5

反応物 3

HCID 5757EstradiolHCID 7918Acetic AnhydrideHCID 21584124Propan-2-one--dichloromethane (1/1)

生成物 1

HCID 3264beta-Estradiol diacetate収率 95%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Under nitrogen, acetic anhydride (50 mL, 264.5 mmol) was added to a solution of estradiol (1a) (20.0 g, 73.43 mmol) in dry pyridine (200 mL). The reaction mixture was stirred at room temperature overnight (16 h). The next morning, analysis by tlc (5% acetone/CH2Cl2) indicated a complete reaction. The mixture was cooled in an ice bath and the excess acetic anhydride quenched by addition of methanol (25 mL). The mixture was stirred at 0° C. for one hour and then allowed to warm to room temperature. The solvents were removed in vacuo and the solid residue crystallized from hot methanol to give the pure diacetate (2a) (24.87 g, 95%).

後処理

  1. customa complete reaction
  2. temperatureThe mixture was cooled in an ice bath
  3. customthe excess acetic anhydride quenched by addition of methanol (25 mL)
  4. stirringThe mixture was stirred at 0° C. for one hour
  5. temperatureto warm to room temperature
  6. customThe solvents were removed in vacuo
  7. customthe solid residue crystallized from hot methanol

出典と根拠

ORDレコード
ord-52a277e776e947bc82b54159aa408f4e
出典データセット
uspto-grants-2003_07
特許番号
US06593321B2

関連ノート

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