2-Ethylhexyl nitrate → HCID 9929531、化合物

HRID 362233ノート

反応式

HRID 362233 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-85ed39f3c7184c94a19fc87157123eb7
出典データセット
uspto-grants-1999_02
特許番号
US05869475

反応ノート

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