Formaldehyde → 3beta-Hydroxymethoxy-androsten-17-one acetate

HRID 356591

反応式

HRID 356591 の反応式
[CH3:1][C@@:2]12[C:10](=[O:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH:13]=[C:14]3[CH2:19][C@@H:18]([OH:20])[CH2:17][CH2:16][C@:15]3([CH3:21])[C@H:5]1[CH2:4][CH2:3]2.[H-].[Na+].[C:24]([O:27]CCl)(=[O:26])[CH3:25].[C:30](Cl)(=[O:32])C.C=O>C1COCC1.[Cl-].[Cl-].[Zn+2].O>[C:24]([OH:27])(=[O:26])[CH3:25].[OH:32][CH2:30][O:20][C@H:18]1[CH2:17][CH2:16][C@@:15]2([CH3:21])[CH:14]([CH2:13][CH2:12][C@@H:6]3[C@@H:5]2[CH2:4][CH2:3][C@@:2]2([CH3:1])[C@H:7]3[CH:8]=[CH:9][C:10]2=[O:11])[CH2:19]1

参加物

9

反応物 5

HCID 712FormaldehydeHCID 5881DehydroepiandrosteroneHCID 6367Acetyl chlorideHCID 24758Sodium hydride2 回HCID 69366Chloromethyl acetate

生成物 1

HCID 1317209423beta-Hydroxymethoxy-androsten-17-one acetate

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of dehydroepiandrosterone (2.88 g, 10 mmol) in THF (100 mL) is added sodium hydride (11 mmol, 60% in oil) at room temperature under an argon atmosphere. When all the sodium hydride has reacted, chloromethyl acetate (prepared from acetyl chloride and formaldehyde (or derivative) using ZnCl2 as catalyst) is added and the mixture is heated for a few hours. After cooling, the mixture is poured into water and extracted with ethyl acetate. The organic phase is then washed with water, dried, filtered and evaporated to dryness to give the desired compound.

後処理

  1. additionis added
  2. temperaturethe mixture is heated for a few hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is then washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated to dryness

出典と根拠

ORDレコード
ord-16c78ee6ebb64ca5bf1cc7df87333e49
出典データセット
uspto-grants-1998_11
特許番号
US05837700

関連ノート

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