Water → HCID 10542413, compound

HRID 1834960Notes

Reaction equation

HRID 1834960 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH2:20][OH:21])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:22])[CH2:3]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.O>CC(C)=O>[CH3:13][C@:12]12[CH2:14][CH2:15][C@H:16]3[C@@H:7]([CH2:6][CH2:5][C@@H:4]4[C@:17]3([CH:20]=[O:21])[CH2:18][CH2:19][C:2](=[O:1])[CH2:3]4)[C@@H:8]1[CH2:9][CH2:10][C:11]2=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 70615006HCID 70615006, compoundHCID 131709961Jones' reagent

Product 1

HCID 10542413HCID 10542413, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 3β,19-dihydroxy-5α-androstan-17-one in acetone chilled to 10° C. is added exactly two equivalents of Jones reagent. After standing for 15 minutes the upper acetone layer is poured into water with vigorous stirring. The solid which forms is filtered, air dried and crystallized from hexane to yield 5α-androstane-3,17,19-trione.

Workup

  1. filtrationThe solid which forms is filtered
  2. customair dried
  3. customcrystallized from hexane

Sources & evidence

ORD record
ord-92f227180abf4c3d98ed613295ef8841
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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