2-Ethylhexyl nitrate → HCID 9929531, 화합물

HRID 362233노트

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HRID 362233 반응식
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]

참가 물질

5

반응물 3

HCID 628232-Ethylhexyl nitrateHCID 11142115HCID 11142115, 화합물HCID 23665647Potassium tert-butoxide

생성물 1

HCID 9929531HCID 9929531, 화합물

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-85ed39f3c7184c94a19fc87157123eb7
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05869475

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