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

HRID 1834970Notes

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

Participants

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

waitthe mixture left
waitstanding for an additional 20 minutes
filtrationThe solid which forms is collected by filtration, air
customdried
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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