trans-1,2-Diacetoxy-1,2-dihydrobenzocyclobutene → 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

HRID 647649Notes

Reaction equation

HRID 647649 reaction equation
[C:1]([O:4][C@@H:5]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C@H:6]1[O:13][C:14](=[O:16])[CH3:15])(=[O:3])[CH3:2].[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>[C:14]([O:13][CH:6]1[C:7]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH:26]2[CH:27]1[C:18](=[O:17])[C:19]1[C:20]3([S:36][CH2:35][CH2:34][S:33]3)[CH2:21][CH:22]([C:29]([O:31][CH3:32])=[O:30])[CH2:23][C:24]=1[C:25]2=[O:28])(=[O:16])[CH3:15]

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 20283276Methyl 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'-carboxylateYield 62%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 0.757 g (3.4 mmol) of trans-1,2-diacetoxy-1,2-dihydrobenzocyclobutene and 0.970 g (3.1 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 100 ml of dry xylene was stirred and heated under reflux under an atmosphere of nitrogen for 1 hour. The mixture was evaporated to dryness and the resulting brown oil was triturated with 10 ml of diethyl ether, cooled and filtered to give 1.02 g (61.5%) 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 in the form of a pale yellow solid of melting point 174°-175° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux under an atmosphere of nitrogen for 1 hour
  3. customThe mixture was evaporated to dryness
  4. customthe resulting brown oil was triturated with 10 ml of diethyl ether
  5. temperaturecooled
  6. filtrationfiltered

Sources & evidence

ORD record
ord-80a64b29950448eebe150f425f07fe79
Source dataset
uspto-grants-1983_10
Patent number
US04409391

Reaction notes

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