4-Toluenesulfonyl chloride → 3beta-Toluene-p-sulphonyloxy-5alpha-pregn-16-ene-11,20-dione

HRID 1606485Notes

Reaction equation

HRID 1606485 reaction equation
[OH:1][C@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[C:17](=[O:23])[CH2:16][C@@:15]2([CH3:24])[C@H:8]3[CH2:9][CH:10]=[C:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>N1C=CC=CC=1>[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31]([O:1][C@H:2]2[CH2:21][CH2:20][C@@:19]3([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]4[C@@H:18]3[C:17](=[O:23])[CH2:16][C@@:15]3([CH3:24])[C@H:8]4[CH2:9][CH:10]=[C:11]3[C:12](=[O:14])[CH3:13])[CH2:3]2)(=[O:33])=[O:32])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 705834293beta-Hydroxy-5alpha-pregn-16-ene-11,20-dione

Product 1

HCID 867333133beta-Toluene-p-sulphonyloxy-5alpha-pregn-16-ene-11,20-dioneYield 97.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3β-hydroxy-5α-pregn-16-ene-11,20-dione (39.6 g) in dry pyridine (165 ml.) was treated with toluene-p-sulphonyl chloride (43.9 g.) to give 3β-toluene-p-sulphonyloxy-5α-pregn-16-ene-11,20-dione (56.7 g.) m.p. 147°-151°. A portion (10.7 g.) of this material was crystallised from ethyl acetate-petrol to give the pure toluenesulphonate (9.2 g.) as plates m.p. 154°-155°, [α]D + 42.8° (c 1.2).

Sources & evidence

ORD record
ord-fe0c89e070aa4420a32a0c3e86dd92ff
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

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