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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 1447477
Notes
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Reaction equation

HRID 1447477 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-793fbaf5480047b5bd7bf3bdc16335a4
Source dataset
uspto-grants-1982_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04316985

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes