Ethylene Glycol → 3a-Methyl-6-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione

HRID 2358277Notes

Reaction equation

HRID 2358277 reaction equation
[CH3:1][C:2]12[CH2:18][CH2:17][C:16]3[CH:7]([O:8][CH2:9][C:10]4[C:15]=3[CH2:14][CH2:13][C:12](=[O:19])[CH:11]=4)[CH:6]1[CH2:5][CH2:4][C:3]2=[O:20].[CH2:21](O)[CH2:22][OH:23].Cl.[NH+]1C=CC=CC=1.C(OCC)(=[O:34])C>C1C=CC=CC=1>[CH3:1][C:2]12[C:3](=[O:20])[CH2:4][CH2:5][CH:6]1[CH:7]1[C:16]([CH2:17][CH2:18]2)=[C:15]([CH2:14][CH2:13][C:12]2([CH3:11])[O:23][CH2:22][CH2:21][O:19]2)[C:10](=[O:34])[CH2:9][O:8]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 8857Ethyl AcetateHCID 21584435Pyridinium hydrochlorideHCID 6845741913-Methyl-1,8,11,12,13,14,15,16-octahydro-2H,6H-7-oxa-cyclopenta[a]phenanthrene-3,17-dione

Product 1

HCID 684591043a-Methyl-6-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 13-methyl-1,8,11,12,13,14,15,16-octahydro-2H,6H-7-oxa-cyclopenta[a]phenanthrene-3,17-dione (1.55 g, 5.7 mmol), ethylene glycol (0.32 mL, 5.7 mmol) and pyridinium hydrochloride (0.66 g, 5.7 mmol) in benzene (28.5 mL) was refluxed with a Dean-Stark apparatus for 3 h. The reaction mixture was diluted with ethyl acetate (100 mL), washed with saturated sodium bisulfate solution, and dried with magnesium sulfate. Flash chromatography using 15% ethyl acetate in hexane yielded the title compound as a white solid.

Workup

  1. washwashed with saturated sodium bisulfate solution
  2. dry with materialdried with magnesium sulfate

Sources & evidence

ORD record
ord-7b22d9f19105487191e939ad5cfb7193
Source dataset
uspto-grants-2010_07
Patent number
US07763648B2

Reaction notes

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