2-Ethylhexyl nitrate → HCID 9929531、化合物

HRID 1290305ノート

反応式

HRID 1290305 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(C(CCCC)C[O:35][N+:36]([O-])=[O:37])C>C(O)(C)(C)C>[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

5

反応物 3

HCID 628232-Ethylhexyl 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 1

HCID 6386tert-Butanol溶媒

実験手順

Potasium tert-butoxide (7.6 g, 67.8 mM) and (20S)-20-hydroxymethylpregn-4-en-3-one (6.6 g, 20 mM) are combined in tert-butanol and heated at reflux temperature for 120 minutes. 2-ethylhexylnitrate (3.56 ml, 20 mM) is then added in one continuous portion. After 10 minutes, the reaction vessel is cooled to room temperature. The reaction is then quenched with acetic acid (9 ml) and stirred overnight. After diluting with dichloromethane (200 mL), the solids are removed, washed, and combined 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. temperatureheated
  2. temperatureat reflux temperature for 120 minutes
  3. customThe reaction is then quenched with acetic acid (9 ml)
  4. additionAfter diluting with dichloromethane (200 mL)
  5. customthe solids are removed
  6. washwashed
  7. customsubsequently purified
  8. customto give
  9. customcrystallized (20S)-20-hydroxymethyl-4-nitropregn-4-en-3-one

出典と根拠

ORDレコード
ord-956b2aa41f12408285da3e0ecccd3095
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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