p-Toluenesulfonic acid → HCID 86741365, compound

HRID 1906503Notes

Reaction equation

HRID 1906503 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C@H:9]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C:19](=[O:21])[CH3:20])[CH2:10]1.[C:31]1(C)C=[CH:35][C:34](S(O)(=O)=O)=[CH:33][CH:32]=1.C(=O)(O)[O-:43].[Na+]>O1C=CCCC1>[O:43]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1[O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C@H:9]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C:19](=[O:21])[CH3:20])[CH2:10]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 86741366HCID 86741366, compound

Product 1

HCID 86741365HCID 86741365, compound

Reagents, catalysts & solvents 1

HCID 80803,4-dihydro-2H-pyranSolvent

Procedure

A solution of pregn-5-en-20-one-3β-yl 6-hydroxyhexyl ether (6.22 g) and p-toluenesulfonic acid (20 mg) in dihydropyran (100 ml) was stirred at room temperature for 18 hours. Solid sodium bicarbonate (1 g) was added and the mixture stirred for 30 minutes. The mixture was filtered through a pad of silica gel which was subsequently washed with 50% ethyl acetate in hexanes. The solvent was removed by rotoevaporation to give the product as a clear colorless oil. TLC data and Rf values for compounds A-D are given in the above Table.

Workup

  1. filtrationThe mixture was filtered through a pad of silica gel which
  2. washwas subsequently washed with 50% ethyl acetate in hexanes
  3. customThe solvent was removed by rotoevaporation

Sources & evidence

ORD record
ord-7b0a8c811a64433c97ae508eed441e61
Source dataset
uspto-grants-1987_03
Patent number
US04652553

Reaction notes

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