Ethylene Glycol → HCID 70505977, compound

HRID 2418138Notes

Reaction equation

HRID 2418138 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[C@@H:12]3[CH2:25][C@@H:13]3[C:14]2=[O:24])[CH2:6]1)(=[O:3])[CH3:2].[CH2:26](O)[CH2:27][OH:28].C(OCC)(OCC)OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.CCOCC.N1C=CC=CC=1>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[C@@H:12]3[CH2:25][C@@H:13]3[C:14]32[O:28][CH2:27][CH2:26][O:24]3)[CH2:6]1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 12834728HCID 12834728, compound

Product 1

HCID 70505977HCID 70505977, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 105 g of 3β-acetoxy-15β,16β-methylene-5-androsten-17-one in 1.05 l of methylene chloride was combined with 315 ml of ethylene glycol, 210 ml of triethyl orthoformate, and 10.5 g of p-toluene-sulfonic acid and agitated for 1 hour at room temperature. The reaction solution was combined with 40 ml of pyridine and diluted with ether, then washed with water, dried, and evaporated. The residue was triturated with pentane and vacuum-filtered, thus producing 109 mg of 3β-acetoxy-17,17-ethylenedioxy-15β,16β-methylene-5-androstene, mp 177°-178.5° C.

Workup

  1. washwashed with water
  2. customdried
  3. customevaporated
  4. customThe residue was triturated with pentane
  5. filtrationvacuum-filtered

Sources & evidence

ORD record
ord-c7188e6a637e4a558293a6a8770e4e7d
Source dataset
uspto-grants-1984_09
Patent number
US04472310

Reaction notes

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