Ethylene Glycol → HCID 15838160, compound

HRID 1603326Notes

Reaction equation

HRID 1603326 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:14](=[O:23])[CH2:13][CH2:12]4)[C@H:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30](=[O:32])[CH3:31])[CH2:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2].[CH2:33](O)[CH2:34][OH:35].C(OC)(OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[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:14]3([O:35][CH2:34][CH2:33][O:23]3)[CH2:13][CH2:12]4)[C@H:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30](=[O:32])[CH3:31])[CH2:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 158381593-Acetoxy-7alpha-(5-acetoxypentyl)-estra-1,3,5(10)-trien-17-one

Product 1

HCID 15838160HCID 15838160, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 63.9 g of 3-acetoxy-7α-(5-acetoxypentyl)-estra-1,3,5(10)-trien-17-one in 460 ml of dichloromethane is stirred with 460 ml of ethylene glycol, 155 ml of trimethyl orthoformate and 1.2 g of para-toluenesulfonic acid for 3 hours at a bath temperature of 50° C. Then, it is diluted with dichloromethane, washed with sodium bicarbonate and common salt solution and dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/ethyl acetate. 63.2 g of 3-acetoxy-7α-(5-acetoxypentyl)-17,17-ethylenedioxy-estra-1,3,5(10)-triene is obtained as oil.

Workup

  1. washwashed with sodium bicarbonate and common salt solution
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customchromatographed on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-f7f832a1ea12427fa9f8c972e420285e
Source dataset
uspto-grants-1999_11
Patent number
US05986115

Reaction notes

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