Hydrochloric Acid → HCID 57092259, compound

HRID 1703199Notes

Reaction equation

HRID 1703199 reaction equation
[OH:1][C@@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:4]([C@@H:5]([OH:29])[CH2:6][C@@H:7]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:19])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])[CH2:3]1.[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1.Cl>N1C=CC=CC=1>[S:36]([O:1][C@@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:4]([C@@H:5]([O:29][S:36]([C:33]3[CH:34]=[CH:35][C:30]([CH3:40])=[CH:31][CH:32]=3)(=[O:38])=[O:37])[CH2:6][C@@H:7]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:19])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:17])[CH3:18])[CH2:3]1)([C:33]1[CH:34]=[CH:35][C:30]([CH3:40])=[CH:31][CH:32]=1)(=[O:38])=[O:37]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 11361671HCID 11361671, compound

Product 1

HCID 57092259HCID 57092259, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.5 g of 3α,6α-dihydroxy-5β-cholest-24-ene and 10.2 g of ρ-toluenesulfonyl chloride were dissolved in 90 ml of dry pyridine and then kept in a refrigerator for 48 hours. The mixture was poured into 300 ml of ice-water and the pH adjusted to 3 by adding concentrated HCl. After stirring for 30 minutes, the precipitate was removed by filtration, washed 4 times with 100 ml portions of water and dissolved in 300 ml of chloroform. The chloroform solution was washed with 30 ml of 5% sodium bicarbonate solution, four times with 50 ml of water solution, and dried. The solvent was evaporated and the residue dried. The yield was 5.1 g of a white solid (83%) identified from ir and nmr data as 3α,6α-ditosyloxy-5β-cholest-24-ene.

Workup

  1. customthe precipitate was removed by filtration
  2. washwashed 4 times with 100 ml portions of water
  3. dissolutiondissolved in 300 ml of chloroform
  4. washThe chloroform solution was washed with 30 ml of 5% sodium bicarbonate solution, four times with 50 ml of water solution
  5. customdried
  6. customThe solvent was evaporated
  7. customthe residue dried

Sources & evidence

ORD record
ord-7900f029ad5e4f08977b133855aa9914
Source dataset
uspto-grants-1982_09
Patent number
US04351767

Reaction notes

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