Methyl 1-acetylamino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate → Methyl 1-acetylamino-2-chloro-6,7,8,9-tetrahydrodibenzofuran-4-carboxylate
Reaction equation
[C:1]([NH:4][C:5]1[C:13]2[CH:12]3[CH2:14][CH2:15][CH2:16][CH2:17][CH:11]3[O:10][C:9]=2[C:8]([C:18]([O:20][CH3:21])=[O:19])=[CH:7][C:6]=1[Cl:22])(=[O:3])[CH3:2]>C1C=CC=CC=1>[C:1]([NH:4][C:5]1[C:13]2[C:12]3[CH2:14][CH2:15][CH2:16][CH2:17][C:11]=3[O:10][C:9]=2[C:8]([C:18]([O:20][CH3:21])=[O:19])=[CH:7][C:6]=1[Cl:22])(=[O:3])[CH3:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 1 g methyl 1-acetylamino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate and 1 g of dichlorodicyanoquinone in 15 ml of benzene is stirred and heated at 80° C in a sealed tube for 8 hours. The cooled reaction mixture is then diluted with benzene, filtered and evaporated to dryness. Purification by recrystallization from ethyl acetate/hexane gives pure methyl 1-acetylamino-2-chloro-6,7,8,9-tetrahydrodibenzofuran-4-carboxylate.
Workup
- customThe cooled reaction mixture
- filtrationfiltered
- customevaporated to dryness
- customPurification
- customby recrystallization from ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-1db8617e4e21499da3b698e0cfae349c
- Source dataset
- uspto-grants-1993_09
- Patent number
- US05246942
Reaction notes
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