Sulfur Dioxide → HCID 70445983, compound

HRID 652218Notes

Reaction equation

HRID 652218 reaction equation
S(=O)=O.[C:4]([O:7][C@H:8]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C:10](=[CH:11][CH2:12][C@@H:13]3[C@@H:22]2[C@@H:21](O)[CH2:20][C@@:18]2([CH3:19])[C@H:14]3[C@@H:15]3[CH2:29][C@@H:16]3[C:17]2=[O:28])[CH2:9]1)(=[O:6])[CH3:5]>CS(Cl)(=O)=O.CN(C)C=O.CC1C=C(C)N=C(C)C=1.C(OCC)(=O)C>[C:4]([O:7][C@H:8]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C:10](=[CH:11][CH2:12][C@@H:13]3[C:22]2=[CH:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]3[C@@H:15]3[CH2:29][C@@H:16]3[C:17]2=[O:28])[CH2:9]1)(=[O:6])[CH3:5]

Participants

7

Reactant 2

HCID 1119Sulfur DioxideHCID 70046766HCID 70046766, compound

Product 1

HCID 70445983HCID 70445983, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 79532,4,6-TrimethylpyridineSolventHCID 8857Ethyl AcetateSolventHCID 31297Methanesulfonyl chlorideSolvent

Procedure

2.6 ml of a solution of 5% by weight sulphur dioxide in methanesulphonic acid chloride are added to a solution of 1.75 g of 3β-acetoxy-11β-hydroxy-15β,16β-methyleneandrost-5-en-17-one in 10.5 ml of dimethylformamide and 3.5 ml of γ-collidine and the whole is stirred for 20 minutes, the internal temperature being allowed to rise to approximately 45°. While stirring, the mixture, including the precipitate that has formed, is poured onto 17.5 ml of ice-water and stirring is continued for a further 10 minutes. The oil that separates out is taken up in ethyl acetate and washed in succession with saturated sodium chloride solution, ice-cold dilute hydrochloric acid, ice-cold dilute sodium hydroxide solution and again with saturated sodium chloride solution. Evaporation of the solvent yields 3β-acetoxy-15β,16β-methyleneandrosta-5,9(11)-dien-17-one that is uniform according to thin-layer chromatography and is processed further without purification.

Workup

  1. customto rise to approximately 45°
  2. stirringWhile stirring
  3. customhas formed
  4. stirringstirring
  5. waitis continued for a further 10 minutes
  6. washwashed in succession with saturated sodium chloride solution, ice-cold dilute hydrochloric acid, ice-cold dilute sodium hydroxide solution and again with saturated sodium chloride solution
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-fa28453fde0548c5b20f83e61a8adbd1
Source dataset
uspto-grants-1987_06
Patent number
US04670551

Reaction notes

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