Acetic Acid → HCID 9929531、化合物

HRID 1290304ノート

反応式

HRID 1290304 の反応式
CC(C)([O-])C.[K+].[OH:7][CH2:8][C@H:9]([C@@H:11]1[C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:18](=[CH:19][C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)[CH3:10].C([O:35][N+:36]([O-])=[O:37])C(C)C.C(O)(=O)C>C(O)(C)(C)C.ClCCl>[OH:7][CH2:8][C@H:9]([C@@H:11]1[C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:18](=[C:19]([N+:36]([O-:37])=[O:35])[C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)[CH3:10]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 10974Isobutyl nitrateHCID 11142115HCID 11142115、化合物HCID 23665647Potassium tert-butoxide

生成物 1

HCID 9929531HCID 9929531、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 6386tert-Butanol溶媒

実験手順

Potassium tert-butoxide (7.6 g, 67.8 mM), (20S)-20-hydroxymethylpregn-4-en-3-one (6.6 g, 20 mM) in tert-butanol is heated at reflux temperature for 60 minutes under an argon atmosphere. Isobutylnitrate (2.34 ml, 20 mM) is then added in one continuous portion. After 20 minutes of further refluxing, the reaction vessel is cooled to room temperature. Acetic acid (10 ml) is then added, and the reaction vessel stirred for 18 hours, after which the combination is diluted with dichloromethane (200 mL). The solids are removed, washed, and recombined with the washing residue and subsequently purified as described in Example 1 to give crystallized (20S)-20-hydroxymethyl-4-nitropregn-4-en-3-one.

後処理

  1. temperatureat reflux temperature for 60 minutes under an argon atmosphere
  2. customThe solids are removed
  3. washwashed
  4. customsubsequently purified
  5. customto give
  6. customcrystallized (20S)-20-hydroxymethyl-4-nitropregn-4-en-3-one

出典と根拠

ORDレコード
ord-af4e2c58ce77416b821731c998f42c80
出典データセット
uspto-grants-1998_05
特許番号
US05750744

反応ノート

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