Sulfuric Acid → HCID 86733291, compound

HRID 1606353Notes

Reaction equation

HRID 1606353 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.[Br:25]CCO.S(=O)(=O)(O)O.C(=O)(O)[O-].[K+]>CCOCC>[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

6

Reactant 4

HCID 1118Sulfuric AcidHCID 108982-BromoethanolHCID 516893Potassium BicarbonateHCID 86733130HCID 86733130, compound

Product 1

HCID 86733291HCID 86733291, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2α, 3α-Epoxy-5α-pregnane-11,20-dione (660 mg.) was dissolved in ether (70 ml.) and 2-bromoethanol (1 ml.) added to the solution. Concentrated sulphuric acid (0.5 ml.) was then added and the mixture stirred at room temperature for one-half hour. 10% Potassium bicarbonate solution (18 ml.) was added and when effervescence had ceased the aqueous layer was removed and extracted with ether (20 ml.). The combined organic extracts were washed with water (100 ml.), dried over anhydrous sodium sulphate and evaporated in vacuo to a pale yellow oil (794 mg.) which was purified by preparative tlc. The main band (RF ~ 0.3) gave 2β-bromo-3α-hydroxy-5α-pregnane-11,20-dione (230 mg.), m.p. 172°-3°C identical with a previously prepared sample.

Workup

  1. customwas removed
  2. extractionextracted with ether (20 ml.)
  3. washThe combined organic extracts were washed with water (100 ml.)
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated in vacuo to a pale yellow oil (794 mg.) which
  6. customwas purified by preparative tlc

Sources & evidence

ORD record
ord-95ac0dccd39e41dd94ef3f541e9a8962
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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