p-Toluenesulfonic acid → HCID 54372363, compound

HRID 1834954Notes

Reaction equation

HRID 1834954 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[CH2:15][CH2:14][CH2:13]4)[CH2:10][CH2:9][C@H:8]1[CH2:7][C:6](=O)[CH2:5][CH2:4]2.C(S)(S)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.B(F)(F)F.CCOCC>[Ni]>[CH3:17][C@:16]12[CH2:18][CH2:19][C@H:20]3[C@@H:11]([CH2:10][CH2:9][C@@H:8]4[C@:3]3([CH2:2][OH:1])[CH2:4][CH2:5][CH2:6][CH2:7]4)[C@@H:12]1[CH2:13][CH2:14][CH2:15]2

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8000Boron trifluoride etherateHCID 336451,1-EthanedithiolHCID 70614884HCID 70614884, compound

Product 1

HCID 54372363HCID 54372363, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

The 3-deoxy series of 5α-androstan-19ols is prepared by converting the 19-hydroxy-5α-androstan-3-one to its 3-ethylenethioketal by reaction with ethanedithiol and an acid catalyst, such as p-toluenesulfonic acid or boron trifluoride etherate. The ethylenethioketal is then desulfurized with Raney nickel to yield the 5α-androstan-19-ol. A Jones oxidation or Pfitzner-Moffatt oxidation results in the formation of the corresponding 5α-androstan19-one.

Sources & evidence

ORD record
ord-f61b5b22f6e84244bec294407e622791
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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