trans-1,2-Diacetoxy-1,2-dihydrobenzocyclobutene → Rac-3'-acetoxy-3'-acetyl-1',2',3',4',5',12'-hexahydro-5',12'-dioxospiro-[1,3-dithiolane-2,1'-naphthacene]

HRID 647657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 647657
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.[C:17]([O:20][C:21]1([C:37](=[O:39])[CH3:38])[CH2:30][C:29]2[C:28](=[O:31])[CH:27]=[CH:26][C:25](=[O:32])[C:24]=2[C:23]2([S:36][CH2:35][CH2:34][S:33]2)[CH2:22]1)(=[O:19])[CH3:18]>C1(C)C(C)=CC=CC=1>[C:17]([O:20][C:21]1([C:37](=[O:39])[CH3:38])[CH2:30][C:29]2[C:28](=[O:31])[C:27]3[C:26](=[CH:6][C:7]4[C:8]([CH:5]=3)=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:25](=[O:32])[C:24]=2[C:23]2([S:36][CH2:35][CH2:34][S:33]2)[CH2:22]1)(=[O:19])[CH3:18]

Komponenten

4

Edukt 2

HCID 13264175trans-1,2-Diacetoxy-1,2-dihydrobenzocyclobuteneHCID 20283284Rac-3'-acetoxy-3'-acetyl-1',2',3',4',5',8'-hexahydro-5',8'-dioxospiro[1,3-dithiolane-2,1'-naphthalene]

Produkt 1

HCID 20283303Rac-3'-acetoxy-3'-acetyl-1',2',3',4',5',12'-hexahydro-5',12'-dioxospiro-[1,3-dithiolane-2,1'-naphthacene]Ausbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixture of 0.825 g (0.00375 mol) of trans-1,2-diacetoxy-1,2-dihydrobenzocyclobutene and 1.20 g (0.0034 mol) of rac-3'-acetoxy-3'-acetyl-1',2',3',4',5',8'-hexahydro-5',8'-dioxospiro[1,3-dithiolane-2,1'-naphthalene] [prepared as described in Example 5(A)] in 65 ml of xylene was stirred and heated under reflux under an atmosphere of nitrogen for 16 hours. The solution was evaporated to dryness and the residue was stirred with 20 ml of diethyl ether and filtered to give 1.259 g (82%) of rac-3'-acetoxy-3'-acetyl-1',2',3',4',5',12'-hexahydro-5',12'-dioxospiro[1,3-dithiolane-2,1'-naphthacene] in the form of a bright yellow solid of melting point 239°-241° C.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux under an atmosphere of nitrogen for 16 hours
  3. customThe solution was evaporated to dryness
  4. stirringthe residue was stirred with 20 ml of diethyl ether
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-cd5103c0efe746858140b008cd2e25d7
Quelldatensatz
uspto-grants-1983_10
Patentnummer
US04409391

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