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HRID362231

反应详情

EQUATION

反应方程式

HRID 362231 的结构方程式

REACTANTS

反应物

4
结构：CC(=O)O
HCID176

Acetic Acid

C2H4O2

结构：CC(C)O[N+](=O)[O-]
HCID15575

Nitric acid, 1-methylethyl ester

C3H7NO3

结构：C[C@H](CO)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
HCID11142115

未命名化合物

结构：CC(C)(C)[O-].[K+]
HCID23665647

2-Methyl-2-propanol, potassium salt

C4H9KO

PRODUCTS

生成物

1
结构：C[C@H](CO)[C@H]1CC[C@H]2[C@@H]3CCC4=C([N+](=O)[O-])C(=O)CC[C@]4(C)[C@H]3CC[C@]12C
HCID9929531

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

2
结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

结构：CC(C)(C)O
溶剂HCID6386

tert-Butyl alcohol

C4H10O

PROCEDURE

实验过程

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.

WORKUP

后处理

  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