HCID 86735750, compound → HCID 70524827, compound

HRID 839467Notes

Reaction equation

HRID 839467 reaction equation
[F:1][C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]3(SC3C=CC=CC=3)[S:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:36])[CH:4]=[CH:5][C:6](=[O:35])[CH:7]=1>C(C1C=CC=CC=1CC)C>[F:1][C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH:14]=[C:15]3[S:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:36])[CH:4]=[CH:5][C:6](=[O:35])[CH:7]=1

Participants

3

Reactant 1

HCID 86735750HCID 86735750, compound

Product 1

HCID 70524827HCID 70524827, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 86571,2-DiethylbenzeneSolvent

Conditions

Temperature
190 °C

Procedure

A suspension of 3.0 g of 9-fluoro-11β-hydroxy-17,17-bis(phenylthio)androsta-1,4-dien-3-one in 150 ml of diethylbenzene is stirred at 190° C for 45 minutes. The solution is cooled at 0° C and a solid crystallizes. This is filtered and dried in vacuo to give 2.3 g of material. Recrystallization from chloroform-methanol gives 1.1 g of the title compound, melting point 250°-251° C (dec.), with consistent spectral data.

Workup

  1. temperatureThe solution is cooled at 0° C
  2. customa solid crystallizes
  3. filtrationThis is filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-11268aaae408418dbeaa1094cf4b1608
Source dataset
uspto-grants-1978_06
Patent number
US04094840

Reaction notes

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