2-Ethylhexyl nitrate → HCID 9929531, compound

HRID 362233Notes

Reaction equation

HRID 362233 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

HCID 9929531HCID 9929531, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-85ed39f3c7184c94a19fc87157123eb7
Source dataset
uspto-grants-1999_02
Patent number
US05869475

Reaction notes

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