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Cerate(2-), hexakis(nitrato-kappaO)-, potassium (1:2), (OC-6-11)- → Methyl rac-1',2',3',4',5',8'-hexahydro-5',8'-dioxospiro[1,3-dithiolane-2,4'-naphthalene]-2'-carboxylate

HRID 1074657
Notes
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Reaction equation

HRID 1074657 reaction equation
[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[Ce].C[O:27][C:28]1[CH:37]=[CH:36][C:35]([O:38]C)=[C:34]2[C:29]=1[C:30]1([S:47][CH2:46][CH2:45][S:44]1)[CH2:31][CH:32]([C:40]([O:42][CH3:43])=[O:41])[CH2:33]2>O.C(#N)C.C(OCC)C>[O:27]=[C:28]1[CH:37]=[CH:36][C:35](=[O:38])[C:34]2[CH2:33][CH:32]([C:40]([O:42][CH3:43])=[O:41])[CH2:31][C:30]3([S:44][CH2:45][CH2:46][S:47]3)[C:29]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 407333Cerate(2-), hexakis(nitrato-kappaO)-, potassium (1:2), (OC-6-11)-HCID 20283292Methyl rac-1',2',3',4'-tetrahydro-5',8'-dimethoxyspiro[1,3-dithiolane-2,4'-naphthalene]-2'-carboxylate

Product 1

HCID 20283295Methyl rac-1',2',3',4',5',8'-hexahydro-5',8'-dioxospiro[1,3-dithiolane-2,4'-naphthalene]-2'-carboxylateYield 82.8%

Reagents, catalysts & solvents 3

HCID 962Water
Solvent
2×
HCID 3283Diethyl EtherSolvent
HCID 6342AcetonitrileSolvent

Procedure

A solution of 4.90 g (0.009 mol) of ammonium ceric nitrate in 20 ml of water was added to a stirred solution of 1.20 g (0.0035 mol) of methyl rac-1',2',3',4'-tetrahydro-5',8'-dimethoxyspiro[1,3-dithiolane-2,4'-naphthalene]-2'-carboxylate in 100 ml of acetonitrile. The mixture was stirred at room temperature for 5 minutes, then diluted with 100 ml of water and extracted with three 200 ml portions of diethyl ether. The combined diethyl ether extracts were washed with water, dried and evaporated to yield 1.23 g of crude product in the form of an orange gum. This was taken up in diethyl ether and crystallised to yield 0.90 g (82%) of methyl rac-1',2',3',4',5',8'-hexahydro-5',8'-dioxospiro[1,3-dithiolane-2,4'-naphthalene]-2'-carboxylate in the form of a bright orange solid of melting point 140°-141° C.

Workup

  1. extractionextracted with three 200 ml portions of diethyl ether
  2. washThe combined diethyl ether extracts were washed with water
  3. customdried
  4. customevaporated
  5. customto yield 1.23 g of crude product in the form of an orange gum
  6. customcrystallised

Sources & evidence

ORD record
ord-e270792959694afdbee61a4c8619e6c3
Source dataset
uspto-grants-1983_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04393221

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes