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19-Trimethylsiloxy-5alpha-androstane-3beta,17beta-diol → 19-Trimethylsiloxy-5alpha-androstane-3,17-dione

HRID 1834970
Notes
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Reaction equation

HRID 1834970 reaction equation
[CH3:1][Si:2]([CH3:26])([CH3:25])[O:3][CH2:4][C@@:5]12[C@@H:22]3[C@H:13]([C@H:14]4[C@@:18]([CH2:20][CH2:21]3)([CH3:19])[C@@H:17]([OH:23])[CH2:16][CH2:15]4)[CH2:12][CH2:11][C@H:10]1[CH2:9][C@@H:8]([OH:24])[CH2:7][CH2:6]2.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:25][Si:2]([CH3:1])([CH3:26])[O:3][CH2:4][C@@:5]12[C@@H:22]3[C@H:13]([C@H:14]4[C@@:18]([CH2:20][CH2:21]3)([CH3:19])[C:17](=[O:23])[CH2:16][CH2:15]4)[CH2:12][CH2:11][C@H:10]1[CH2:9][C:8](=[O:24])[CH2:7][CH2:6]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 2280149619-Trimethylsiloxy-5alpha-androstane-3beta,17beta-diolHCID 131709961Jones' reagent

Product 1

HCID 2280152719-Trimethylsiloxy-5alpha-androstane-3,17-dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
10 °C

Procedure

19-Trimethylsiloxy-5α-androstane-3β,17β-diol is dissolved in acetone and chilled to 10° C. Jones reagent is added with stirring over a period of 5 minutes and the mixture left standing for an additional 20 minutes. The acetone layer is poured onto water with vigorous stirring. The solid which forms is collected by filtration, air dried and crystallized from an acetone-hexane solution to yield 19-trimethylsiloxy-5α-androstane-3,17-dione.

Workup

  1. waitthe mixture left
  2. waitstanding for an additional 20 minutes
  3. filtrationThe solid which forms is collected by filtration, air
  4. customdried
  5. customcrystallized from an acetone-hexane solution

Sources & evidence

ORD record
ord-888799ce0873422a860e6f2f9ac77d9a
Source dataset
uspto-grants-1978_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04071625

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes