Chlorosulfonic acid → HCID 13145955, compound

HRID 851290Notes

Reaction equation

HRID 851290 reaction equation
ClS(O)(=O)=O.[F:6][C@H:7]1[C:24]2[C@:19]([CH3:26])([CH2:20][CH2:21][C:22](=[O:25])[CH:23]=2)[C@:18]2(O)[C@H:9]([C@H:10]3[C@@:14]([CH2:16][CH2:17]2)([CH3:15])[C:13](=[O:28])[CH2:12][CH2:11]3)[CH2:8]1>C(Cl)Cl>[F:6][C@H:7]1[C:24]2[C@:19]([CH3:26])([CH2:20][CH2:21][C:22](=[O:25])[CH:23]=2)[C:18]2[C@H:9]([C@H:10]3[C@@:14]([CH2:16][CH:17]=2)([CH3:15])[C:13](=[O:28])[CH2:12][CH2:11]3)[CH2:8]1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 13145953HCID 13145953, compound

Product 1

HCID 13145955HCID 13145955, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chlorosulfonic acid (2.0 ml) is added to methylene chloride (50 ml) containing 6β-fluoro-9α-hydroxyandrost-4-ene-3,17-dione (III, Example 2, 5.2 g) previously cooled to -20°. After 1.25 hr, the cold solution is quenched by adding slowly water (2 ml). The organic mixture is then washed with water, aqueous sodium carbonate, dried over sodium sulfate, and the organic solvent removed under reduced pressure to give the title compound. Rf (ethyl acetate/hexane, 1/1)=0.5; NMR (CDCl3) 0.9, 1.5, 5.1, 5.6 and 5.9 δ.

Workup

  1. temperaturepreviously cooled to -20°
  2. customthe cold solution is quenched
  3. additionby adding slowly water (2 ml)
  4. washThe organic mixture is then washed with water, aqueous sodium carbonate
  5. dry with materialdried over sodium sulfate
  6. customthe organic solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b017b5a8360847b194f7489bad4aec4e
Source dataset
uspto-grants-1983_05
Patent number
US04383947

Reaction notes

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