Water → HCID 25749221, compound

HRID 1576348Notes

Reaction equation

HRID 1576348 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:20])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22].O>N1C=CC=CC=1>[C:21]([O:1][C:2]1[CH:19]=[CH:18][C:17]2[C@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:20])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 11869537HCID 11869537, compound

Product 1

HCID 25749221HCID 25749221, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Hydroxy-9β-oestra-1,3,5(10)-trien-17-one (370 mg., 1.4 mmole) was treated with acetic anhydride (3 ml.) in pyridine (3 ml.) at steam-bath temperature for 45 min. The cooled solution was poured into water (50 ml.), and extracted with ether (50 ml.). The ether extract was washed with 2N-sulphuric acid (25 ml.), then water (2 × 25 ml.) and the solvent evaporated in vacuo to give the title compound as a chromatographically pure oil (390 mg., 90%), υmax. 1758, 1735 and 1200 cm. -1.

Workup

  1. extractionextracted with ether (50 ml.)
  2. extractionThe ether extract
  3. washwas washed with 2N-sulphuric acid (25 ml.)
  4. customwater (2 × 25 ml.) and the solvent evaporated in vacuo

Sources & evidence

ORD record
ord-f6b76f140c7a42098dc01d7b2cac9af3
Source dataset
uspto-grants-1976_09
Patent number
US03980681

Reaction notes

Loading…