p-Toluenesulfonic acid → HCID 68147543, compound

HRID 1606271Notes

Reaction equation

HRID 1606271 reaction equation
[C:1]([O:4][C:5]1[C:22]2[C@@H:21]3[C@@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:23])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:24][C:25](=[O:27])[CH3:26])[CH:6]=1)(=[O:3])[CH3:2].[C:28](OC(C)=C)(=[O:30])[CH3:29].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:1]([O:4][C:5]1[C:22]2[C@@H:21]3[C@@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16]([O:23][C:28](=[O:30])[CH3:29])=[CH:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:24][C:25](=[O:27])[CH3:26])[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7916Isopropenyl acetateHCID 68146911HCID 68146911, compound

Product 1

HCID 68147543HCID 68147543, compound

Conditions

Temperature
125 °C

Procedure

A mixture of 5 g. of rac.-1,3-diacetoxy-8α-estra-1,3,5(10)-trien-17-one, 100 ml. of isopropenyl acetate, and 14.4 g. of p-toluenesulfonic acid is heated for 21 hours under a slight N2 stream to 105° C. After the mixture has been heated to 125° C., 50 ml. of isopropenyl acetate are gradually distilled off. After cooling, 10 ml. of pyridine is added, the mixture is diluted with methylene chloride, washed with saturated sodium bicarbonate solution and water, and dried over sodium sulfate. The solvent is evaporated under vacuum. After chromatography on 260 g. of SiO2, 3 g. of oily rac.-1,3,17-triacetoxy-8α-estra-1,3,5(10),16-tetraene is obtained, which is further processed as the crude product.

Workup

  1. additionA mixture of 5 g
  2. distillationof isopropenyl acetate are gradually distilled off
  3. temperatureAfter cooling
  4. additionof pyridine is added
  5. additionthe mixture is diluted with methylene chloride
  6. washwashed with saturated sodium bicarbonate solution and water
  7. dry with materialdried over sodium sulfate
  8. customThe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-d1cad07377974f45a498c629ece70bd0
Source dataset
uspto-grants-1976_04
Patent number
US03951958

Reaction notes

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