Sodium Hydroxide → Methyl rac-1',2',3',4',5',12'-hexahydro-5',12'-dioxospiro[1,3-dithiolane-2,4'-naphthacene]-2'-carboxylate

HRID 1074667Notes

Reaction equation

C(O[CH:5]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16](OC(=O)C)[CH:15]2[CH:6]1[C:7](=[O:36])[C:8]1[C:9]3([S:35][CH2:34][CH2:33][S:32]3)[CH2:10][CH:11]([C:28]([O:30][CH3:31])=[O:29])[CH2:12][C:13]=1[C:14]2=[O:27])(=O)C.[OH-].[Na+]>CO.O>[O:36]=[C:7]1[C:6]2[C:15](=[CH:16][C:17]3[C:22]([CH:5]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14](=[O:27])[C:13]2[CH2:12][CH:11]([C:28]([O:30][CH3:31])=[O:29])[CH2:10][C:9]3([S:32][CH2:33][CH2:34][S:35]3)[C:8]1=2

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 26.5 mg (0.05 mmol) of methyl rac-1',2',3',4',5',5a',6',11',11a',12'-decahydro-6',11'-diacetoxy-5',12'-dioxospiro[1,3-dithiolane-2,4'-naphthacene]-2'-carboxylate and 5 mg (0.125 mmol) of sodium hydroxide in 2 ml of methanol was stirred at 20° C. for 1.5 hours. The mixture was then diluted with 10 ml of water and extracted with two 10 portions of dichloromethane. The combined dichloromethane extracts were washed with 10 ml of water, dried over magnesium sulphate and evaporated to dryness to give 15 mg (73%) of methyl rac-1',2',3',4',5',12'-hexahydro-5',12'-dioxospiro[1,3-dithiolane-2,4'-naphthacene]-2'-carboxylate in the form of a bright yellow solid of melting point 216° C.

Workup

extractionextracted with two 10 portions of dichloromethane
washThe combined dichloromethane extracts were washed with 10 ml of water
dry with materialdried over magnesium sulphate
customevaporated to dryness

Sources & evidence

ORD record: ord-964a3a18e36c478a8311edec6cc6f197
Source dataset: uspto-grants-1983_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04393221

Reaction notes

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