Ethylene Glycol → HCID 15086123, compound

HRID 1885559Notes

Reaction equation

HRID 1885559 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][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][C:36](=[O:38])[CH3:37])[CH2:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2].[CH2:39](O)[CH2:40][OH:41].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:41][CH2:40][CH2:39][O:23]3)[CH2:13][CH2:12]4)[C@H:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][C:36](=[O:38])[CH3:37])[CH2:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 150861223-Acetoxy-7alpha-(11-acetoxyundecyl)-1,3,5(10)-estratrien-17-one

Product 1

HCID 15086123HCID 15086123, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7.85 g of 3-acetoxy-7α-(11-acetoxyundecyl)-1,3,5(10)-estratrien-17-one is stirred under reflux in 51 ml of dichloromethane and 51 ml of ethylene glycol with 24 ml of trimethyl orthoformate and 159 mg of p-toluenesulfonic acid for 0.5 hour. For working up purposes, the mixture is diluted with dichloromethane, washed with sodium bicarbonate and sodium chloride solutions, dried over sodium sulfate, concentrated to dryness under vacuum, and chromatographed on silica gel with hexane/ethyl acetate, yielding 6.5 g of pure 3-acetoxy-7α-(11-acetoxyundecyl)-17,17-ethylenedioxy-1,3,5(10)-estratriene, [α]D =13.4°, as an oil.

Workup

  1. washwashed with sodium bicarbonate and sodium chloride solutions
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness under vacuum
  4. customchromatographed on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-e24f30135f1b4ec59ebadff5967b1a5f
Source dataset
uspto-grants-1992_09
Patent number
US05145847

Reaction notes

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