trans-1,2-Diacetoxy-1,2-dihydrobenzocyclobutene → Methyl rac-1',2',3',4',5',12'-hexahydro-5',12'-dioxospiro[1,3-dithiolane-2,4'-naphthacene]-2'-carboxylate

HRID 647656Notes

Reaction equation

HRID 647656 reaction equation
C(O[C@@H:5]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C@H:6]1OC(=O)C)(=O)C.[O:17]=[C:18]1[CH:27]=[CH:26][C:25](=[O:28])[C:24]2[CH2:23][CH:22]([C:29]([O:31][CH3:32])=[O:30])[CH2:21][C:20]3([S:36][CH2:35][CH2:34][S:33]3)[C:19]1=2>C1(C)C(C)=CC=CC=1>[O:17]=[C:18]1[C:27]2[C:26](=[CH:6][C:7]3[C:8]([CH:5]=2)=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:25](=[O:28])[C:24]2[CH2:23][CH:22]([C:29]([O:31][CH3:32])=[O:30])[CH2:21][C:20]3([S:33][CH2:34][CH2:35][S:36]3)[C:19]1=2

Participants

4

Reactant 2

HCID 13264175trans-1,2-Diacetoxy-1,2-dihydrobenzocyclobuteneHCID 20283295Methyl rac-1',2',3',4',5',8'-hexahydro-5',8'-dioxospiro[1,3-dithiolane-2,4'-naphthalene]-2'-carboxylate

Product 1

HCID 20283279Methyl rac-1',2',3',4',5',12'-hexahydro-5',12'-dioxospiro[1,3-dithiolane-2,4'-naphthacene]-2'-carboxylateYield 60.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 70 mg (0.32 mmol) of trans-1,2-diacetoxy-1,2-dihydrobenzocyclobutene and 66 mg (0.21 mmol) of methyl rac-1',2',3',4',5',8'-hexahydro-5',8'-dioxospiro[1,3-dithiolane-2,4'-naphthalene]-2'-carboxylate [prepared as described in Example 2(A)] in 5 ml of xylene was stirred and heated under reflux under an atmosphere of nitrogen for 23 hours. The mixture was evaporated to dryness and the residue was stirred with 5 ml of diethyl ether and then filtered to give 52 mg (60%) 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

  1. temperatureheated
  2. temperatureunder reflux under an atmosphere of nitrogen for 23 hours
  3. customThe mixture was evaporated to dryness
  4. stirringthe residue was stirred with 5 ml of diethyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-49a4b375d53a4583a4da034f5f5398df
Source dataset
uspto-grants-1983_10
Patent number
US04409391

Reaction notes

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