Acetic Acid → HCID 9929531、化合物

HRID 362231ノート

反応式

HRID 362231 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:34][N+:35]([O-])=[O:36])(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+:35]([O-:36])=[O:34])[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 15575Isopropyl 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 (1.70 g, 15 mM), (20S)-20-hydroxymethylpregn-4-en-3-one (1.65 g, 5 mM) are mixed in tert-butanol and heated at reflux temperature, under argon atmosphere for 90 minutes. The combination is then cooled to room temperature and treated with one continuous portion of isopropylnitrate (0.51 mL, 5 mM). After 18 hours, the contents of the reaction vessel are acidified with 5 ml of acetic acid, and subsequently diluted with dichloromethane. The solids are then removed by filtration and further washed with additional dichloromethane. The filtrate and wash residue are purified as described in Example 1 to give a crystallized (20S)-20-hydroxymethyl-4-nitropregn-4-en-3-one.

後処理

  1. temperatureheated
  2. temperatureat reflux temperature
  3. waitAfter 18 hours
  4. customThe solids are then removed by filtration
  5. washfurther washed with additional dichloromethane
  6. washThe filtrate and wash residue
  7. customare purified

出典と根拠

ORDレコード
ord-4f5032ed46294f4fb250b5b17de458cc
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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