Hydrogen Bromide → HCID 86733291, compound

HRID 1606476Notes

Reaction equation

HRID 1606476 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:20]([CH3:22])([CH2:21][C@@H:2]12)[C@@H:19]1[C@H:8]([C@H:9]2[C@:16]([CH3:24])([CH2:17][C:18]1=[O:23])[C@@H:12]([C:13](=[O:15])[CH3:14])[CH2:11][CH2:10]2)[CH2:7][CH2:6]3.[BrH:25]>C(Cl)(Cl)Cl>[Br:25][C@H:2]1[CH2:21][C@@:20]2([CH3:22])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:19]2[C:18](=[O:23])[CH2:17][C@@:16]2([CH3:24])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:13](=[O:15])[CH3:14])[CH2:4][C@@H:3]1[OH:1]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 86733130HCID 86733130, compound

Product 1

HCID 86733291HCID 86733291, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2α, 3α-Epoxy-5α-pregnane-11,20-dione (502 mg) was dissolved in chloroform (30 ml.) and the solution was treated with hydrobromic acid (48 %, 10 ml.). The mixture was stirred vigorously at room temperature for 30 minutes, and then poured into chloroform. The organic solution was washed with dilute sodium bicarbonate solution, then with water, and was then dried over sodium sulphate and evaporated to give a crystalline residue which was recrystallised from acetone-ether to give 2β-bromo-3α-hydroxy-5α-pregnane-11,20-dione (483 mg.) as colourless crystals, m.p. 206°-210° [α]D + 106°.

Workup

  1. washThe organic solution was washed with dilute sodium bicarbonate solution
  2. dry with materialwith water, and was then dried over sodium sulphate
  3. customevaporated
  4. customto give a crystalline residue which
  5. customwas recrystallised from acetone-ether

Sources & evidence

ORD record
ord-27f96e48e89b405c9e2bfe72a483c64f
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

Loading…