Boron trifluoride → HCID 86735750, compound

HRID 839466Notes

Reaction equation

HRID 839466 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=O)[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:23])[CH:4]=[CH:5][C:6](=[O:22])[CH:7]=1.[C:24]1([SH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.B(F)(F)F>ClCCl.C(O)(=O)C.C(Cl)(Cl)Cl>[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([S:30][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[S:30][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:23])[CH:4]=[CH:5][C:6](=[O:22])[CH:7]=1

Participants

7

Reactant 3

HCID 6356Boron trifluorideHCID 7969ThiophenolHCID 13421116HCID 13421116, compound

Product 1

HCID 86735750HCID 86735750, compoundYield 78.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 9.0 g of 9-fluoro-11β-hydroxyandrosta-1,4-diene-3,17-dione in 50 ml of dichloromethane and 50 ml of glacial acetic acid is stirred with 18.68 g of thiophenol and 7.5 ml of boron trifluoride ethereate at room temperature under nitrogen. After 50 minutes the solution is diluted with 350 ml of chloroform. The chloroform solution is washed successively with water, saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate and evaporated in vacuo to give 11.6 g of an oil. This is dissolved in 1:3 hexane-chloroform and chromatographed on a 200 g-silica gel column. Elution with 1:3 hexane-chloroform and chloroform gives 3.5 of a tlc-homogeneous material. Crystallization from chloroform-methanol gives 2.0 g of the title compound, melting point 249°-250° C (dec.), with consistent spectral data.

Workup

  1. washThe chloroform solution is washed successively with water, saturated sodium bicarbonate solution and water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-ab2344fad2544a8c8ed6678f23ad5768
Source dataset
uspto-grants-1978_06
Patent number
US04094840

Reaction notes

Loading…