4-Toluenesulfonyl chloride → HCID 22791488, compound

HRID 918056Notes

Reaction equation

HRID 918056 reaction equation
[OH:1][C@@H:2]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:20]2[C:19](=[O:25])[CH2:18][C@@:17]2([CH3:26])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:16])[CH2:13][O:14][CH3:15])[CH2:3]1.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>N1C=CC=CC=1>[CH3:15][O:14][CH2:13][C:12](=[O:16])[C@@H:11]1[C@:17]2([CH3:26])[C@H:8]([C@H:7]3[C@H:20]([C:19](=[O:25])[CH2:18]2)[C@:21]2([CH3:24])[C@H:4]([CH2:3][C@H:2]([O:1][S:33]([C:30]4[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=4)(=[O:35])=[O:34])[CH2:23][CH2:22]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 86733695HCID 86733695, compound

Product 1

HCID 22791488HCID 22791488, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3α-Hydroxy-21-methoxy-5α-pregnane-11,20-dione (1.5 g.) in dry pyridine (7.5 ml.) was treated with toluene p-sulphonyl chloride (1.5 g.) at room temperature overnight. The reaction mixture was then partitioned between 2N-hydrochloric acid and chloroform, washed with water, dried (Na2SO4) and evaporated to give 21-methoxy-3α-(p-toluene sulphonyloxy)-5α-pregnane-11,20-dione (1.55 g.) as a foam.

Workup

  1. customThe reaction mixture was then partitioned between 2N-hydrochloric acid and chloroform
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-4b86384fbba545a98ff93e08b0c47973
Source dataset
uspto-grants-1976_07
Patent number
US03969345

Reaction notes

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