Cyclohexanone → HCID 67865375, compound

HRID 1650788Notes

Reaction equation

HRID 1650788 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.C1(=O)CCCCC1.CC([O-])C.CC([O-])C.CC([O-])C.[Al+3].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.ClCCl.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

8

Reactant 4

HCID 7967CyclohexanoneHCID 11143Aluminum isopropoxideHCID 9855836Potassium sodium tartarateHCID 67865743HCID 67865743, compound

Product 1

HCID 67865375HCID 67865375, compoundYield 66.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

623 mg (E)-3-fluoromethylene-4-androsten-17-beta-ol is dissolved in 25 ml of toluene, mixed with 7 ml of cyclohexanone and three times with 300 mg of aluminum triisopropylate at 160° C. bath temperature on a water separator. After cooling, it is stirred with potassium sodium tartrate for 30 minutes at 60° C., diluted with dichloromethane, washed neutral, dried on sodium sulfate and concentrated. After chromatography on silica gel with hexane/ethyl acetate, 412 mg (E)-3-fluoromethylene-4-androsten-17-one with a melting point of 142°-143° C. is obtained.

Workup

  1. temperatureAfter cooling
  2. washwashed neutral
  3. customdried on sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9663b068ff9f480d87c899a020cdf6d7
Source dataset
uspto-grants-1990_05
Patent number
US04925834

Reaction notes

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