Methanesulfonyl chloride → HCID 10135141, compound

HRID 1576352Notes

Reaction equation

HRID 1576352 reaction equation
[C:1]([O:4][C:5]1[CH:22]=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C@@H:14]([OH:23])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2].[CH3:24][S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1.O>[C:1]([O:4][C:5]1[CH:22]=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C@@H:14]([O:23][S:25]([CH3:24])(=[O:27])=[O:26])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 9818306Estradiol acetate

Product 1

HCID 10135141HCID 10135141, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

3-Acetoxy-oestra-1,3,5(10)-trien-17β-ol (500 mg., 1.6 mmole) in pyridine (2 ml.) was treated at room temperature for 16 hr. with methanesulphonyl chloride (1 ml.). The solution was diluted slowly with water (25 ml.) then the product was extracted into ether (50 ml.). The extract was washed with 2N-sulphuric acid (25 ml.) then water (50 ml.) and the solvent was evaporated in vacuo. Crystallisation of the residue from slightly aqueous methanol gave the title compound in two crops (total 519 mg., 93%), m.p. 120°-122°.

Workup

  1. extractionthe product was extracted into ether (50 ml.)
  2. washThe extract was washed with 2N-sulphuric acid (25 ml.)
  3. customwater (50 ml.) and the solvent was evaporated in vacuo
  4. customCrystallisation of the residue from slightly aqueous methanol

Sources & evidence

ORD record
ord-3af7d9029159402aa80e9f3468a9f585
Source dataset
uspto-grants-1976_09
Patent number
US03980681

Reaction notes

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