Water → HCID 18639277, compound

HRID 1650789Notes

Reaction equation

HRID 1650789 reaction equation
[F:1]/[CH:2]=[C:3]1\[CH:4]=[C:5]2[C@:18]([CH3:21])([CH2:19][CH2:20]\1)[C@@H:17]1[C@H:8]([C@H:9]3[C@@:13]([CH2:15][CH2:16]1)([CH3:14])[C@@H:12]([OH:22])[CH2:11][CH2:10]3)[CH2:7][CH2:6]2.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.O>CC(C)=O>[F:1]/[CH:2]=[C:3]1\[CH:4]=[C:5]2[C@:18]([CH3:21])([CH2:19][CH2:20]\1)[C@@H:17]1[C@H:8]([C@H:9]3[C@@:13]([CH2:15][CH2:16]1)([CH3:14])[C:12](=[O:22])[CH2:11][CH2:10]3)[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 962WaterHCID 67865063HCID 67865063, compoundHCID 131709961Jones' reagent

Product 1

HCID 18639277HCID 18639277, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1200 mg of (Z)-3-fluoromethylene-4-androsten-17-beta-ol is dissolved in 30 ml of acetone and mixed at 0° C. with 1.5 ml of Jones reagent. Then it is added to water, extracted three times with dichloromethane, washed neutral, dried on sodium sulfate and concentrated. After chromatography on silica gel with hexane/ethyl acetate, 842 mg of (Z)-3-fluoromethylene-4-androsten-17-one is obtained with a melting point of 101°-102° C.

Workup

  1. extractionextracted three times with dichloromethane
  2. washwashed neutral
  3. customdried on sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-778addff30bc449bad4484dc073a14d7
Source dataset
uspto-grants-1990_05
Patent number
US04925834

Reaction notes

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