Hydrochloric Acid → HCID 13488078, compound

HRID 1607976Notes

Reaction equation

S(O[C@@H:6]1[C@@:25]2([CH3:26])[C@@H:18]([CH2:19][CH2:20][C@@H:21]2[C:22](=[O:24])[CH3:23])[C@H:17]2[C@@H:8]([C@:9]3([CH3:28])[C:14]([CH2:15][CH2:16]2)=[CH:13][C:12](=[O:27])[CH:11]=[CH:10]3)[CH2:7]1)(C)(=O)=O.C([O-])(=O)C.[K+].Cl>CN(C)P(N(C)C)(N(C)C)=O>[CH3:23][C:22](=[O:24])[C@@H:21]1[C@:25]2([CH3:26])[C@H:18]([C@H:17]3[C@H:8]([CH:7]=[CH:6]2)[C@:9]2([CH3:28])[C:14](=[CH:13][C:12](=[O:27])[CH:11]=[CH:10]2)[CH2:15][CH2:16]3)[CH2:19][CH2:20]1

Participants

Conditions

Temperature: 120 °C

Procedure

12α-Mesyloxypregna-1,4-diene-3,20-dione (3.0 g) was dissolved in 60 ml of hexamethylphosphoramide. To the solution was added 7.2 g of potassium acetate, and the mixture was stirred at 120° C. for 5 hours. To the reaction mixture was added 300 ml of diluted hydrochloric acid, and the whole mixture was extracted with three 200 ml portions of benzene. The extracts were combinedly washed in sequence with diluted hydrochloric acid and water, and dried over anhydrous magnesium sulfate. Low-boiling fractions were distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluent: acetone-n-hexane, 4:6 by volume) to give 1.6 g of pregna-1,4,11(12)-triene-3,20-dione as crystals. The physical properties for the obtained crystal were as follows:

Workup

extractionthe whole mixture was extracted with three 200 ml portions of benzene
washThe extracts were combinedly washed in sequence with diluted hydrochloric acid and water
dry with materialdried over anhydrous magnesium sulfate
distillationwere distilled off under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent: acetone-n-hexane, 4:6 by volume)

Sources & evidence

ORD record: ord-2cc42cf5f468462f91ee6647943b9209
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04867914

Reaction notes

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