Sodium Hydroxide → HCID 86733323, compound

HRID 1606473Notes

Reaction equation

HRID 1606473 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C:21]2=[CH:20][CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2].BrN1C(=[O:33])CCC1=O.Cl(O)(=O)(=O)=O.[OH-].[Na+]>O1CCOCC1.O.C(O)(=O)C>[C:1]([O:4][C@@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@:21]42[O:33][C@H:20]4[CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24247Perchloric AcidHCID 67184N-bromobutanimideHCID 70632676HCID 70632676, compound

Product 1

HCID 86733323HCID 86733323, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

3α-Acetoxy-5α-pregn-9(11)-en-20-one (3 g.) was dissolved in dioxan (300 ml.) and water (75 ml.); N-bromosuccinimide (2.1 g.) was added followed by perchloric acid (60% w/v; 1.05 ml.) in water (30 ml.) and the reaction allowed to stand at room temperature under nitrogen for 5 min. The pH was adjusted to 11.7 with 2N sodium hydroxide and the reaction mixture was allowed to stand at room temperature under nitrogen for a further 15 min; the pH was adjusted to 6 with glacial acetic acid and the mixture was poured into water. The steroid was extracted with ether to give a crystalline solid (3.2 g.); crystallisation from ether-petrol followed by recrystallisation from aqueous methanol gave the title compound m.p. 133°-136°, [α]D + 105°.

Workup

  1. waitto stand at room temperature under nitrogen for a further 15 min
  2. extractionThe steroid was extracted with ether
  3. customto give a crystalline solid (3.2 g.)
  4. customcrystallisation from ether-petrol
  5. customfollowed by recrystallisation from aqueous methanol

Sources & evidence

ORD record
ord-de0c8b159a674e4abe72b11f7eaf03d8
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

Loading…