4-Toluenesulfonyl chloride → HCID 86738209, compound

HRID 1105844Notes

Reaction equation

HRID 1105844 reaction equation
[CH3:1]/[CH:2]=[C:3]1/[CH2:4][CH2:5][C@@H:6]2[C@:20]/1([CH3:21])[CH2:19][CH2:18][C@H:17]1[C@H:7]2[CH2:8][CH:9]=[C:10]2[C@:15]1([CH3:16])[CH2:14][CH2:13][C@H:12]([OH:22])[CH2:11]2.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.C(=O)(O)[O-:35].[Na+]>N1C=CC=CC=1>[CH3:1]/[CH:2]=[C:3]1/[CH2:4][CH2:5][C@@H:6]2[C@:20]/1([CH3:21])[CH2:19][CH2:18][C@H:17]1[C@H:7]2[CH2:8][CH:9]=[C:10]2[C@:15]1([CH3:16])[CH2:14][CH2:13][C@H:12]([OH:22])[CH2:11]2.[CH3:33][C:23]1[CH:28]=[CH:27][C:26]([S:29]([OH:35])(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chloride2×HCID 516892Sodium BicarbonateHCID 11087916HCID 11087916, compound

Product 1

HCID 86738209HCID 86738209, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.80 g (6.0 mmol) (Z)-pregna-5,17(20)-dien-3β-ol in 8 ml of pyridine under a nitrogen atmosphere was added 1.26 g (6.6 mmol) of p-toluenesulfonyl chloride. Precipitation (pyridinium hydrochloride) began after 3 hr. After 19 hr., an additional 1.03 g (5.4 mmol) of p-toluenesulfonyl chloride was added. The reaction was left stirring for 5 days and then was poured into a stirred solution of 150 ml of 5% aqueous sodium bicarbonate cooled to 7°. After 30 min., the precipitate was removed by filtration, the filter cake washed with 2×15 ml of water and then dried over night to a vacuum dessicator (Drierite) at about 1 mm Hg to afford 2.50 g (92%) of crude product suitable for the next step. (Unstable to chromatography). An analytical sample was recrystallized from hexane to give (Z)-pregna-5,17(20)-dien-3β-ol-p-toluenesulfonate as white crystals, mp 119°-119.3°.

Workup

  1. customPrecipitation (pyridinium hydrochloride)
  2. waitAfter 19 hr
  3. waitThe reaction was left
  4. temperaturecooled to 7°
  5. waitAfter 30 min.
  6. customthe precipitate was removed by filtration
  7. washthe filter cake washed with 2×15 ml of water
  8. dry with materialdried over night to a vacuum dessicator (Drierite) at about 1 mm Hg
  9. customto afford 2.50 g (92%) of crude product suitable for the next step
  10. customAn analytical sample was recrystallized from hexane

Sources & evidence

ORD record
ord-33e6b80f5b4140a9af12e1b1d4c82cee
Source dataset
uspto-grants-1982_01
Patent number
US04310467

Reaction notes

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