HCID 22797455, compound → HCID 22797482, compound

HRID 2398005Notes

Reaction equation

HRID 2398005 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])[C@@H:15]([O:21][Si:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[C:7]([CH3:41])[C:6](=[O:42])[CH2:5][CH2:4]2.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:41][C:7]1[C:6](=[O:42])[CH2:5][CH2:4][C@@:3]2([CH:2]=[O:1])[C:8]=1[CH2:9][CH2:10][C@@H:11]1[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]1[CH2:13][CH2:14][C@@H:15]2[O:21][Si:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 22797455HCID 22797455, compoundHCID 131709961Jones' reagent

Product 1

HCID 22797482HCID 22797482, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 19-hydroxy-4-methyl-17β-triphenylsiloxy-androst-4-en-3-one in acetone chilled to 10° C. is added one equivalent of Jones Reagent. After 30 minutes, the acetone layer is decanted and poured onto water with vigorous stirring. The solid is filtered, dried in a vacuum oven and crystallized from hexane to yield 4-methyl-17β-triphenylsiloxy-4-androstene-3,19-dione.

Workup

  1. customthe acetone layer is decanted
  2. additionpoured onto water with vigorous stirring
  3. filtrationThe solid is filtered
  4. customdried in a vacuum oven
  5. customcrystallized from hexane

Sources & evidence

ORD record
ord-07aa3a81f101497da0121f59b8cbe3c6
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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