2-Ethylhexyl nitrate → HCID 9929531, Verbindung

HRID 362233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362233
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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 9929531HCID 9929531, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-85ed39f3c7184c94a19fc87157123eb7
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05869475

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