HCID 13373177, compound → HCID 20563350, compound
Reaction equation
[CH2:1]=[C:2]1[C:15](=[CH2:16])[CH:14]2[O:17][CH:3]1[C:4]1[CH2:5][CH:6]3[CH:11]([CH2:12][C:13]=12)[C:10](=O)[CH:9]=[CH:8][CH:7]3[O:19]S(C)(=O)=O>O1CCCC1>[CH2:16]=[C:15]1[C:2](=[CH2:1])[CH:3]2[O:17][CH:14]1[C:13]1[CH2:12][C:11]3[CH:10]=[CH:9][CH:8]=[C:7]([OH:19])[C:6]=3[CH2:5][C:4]=12Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
876 mg of potassium tert.butylate were added under a nitrogen atmosphere to a solution of 2.37 g of 1,2,3,4,5,8,8a,9,10,10a-decahydro-2,3-dimethylene-1,4-epoxy-8-mesyloxyanthracen-5-one in 40 ml of tetrahydrofuran, there being formed 1,2,3,4,9,10-hexahydro-2,3-dimethylene-1,4-epoxyanthracen-5-ol. After stirring at room temperature for 1 hour, a further 877 mg of potassium tert.butylate were added. The mixture was stirred for a further 45 minutes, 1.32 ml of methyl iodide were added and the resulting mixture was stirred for a further 1 hour. The mixture was treated with 100 ml of aqueous ammonium chloride and extracted three times with 100 ml of diethyl ether each time. After washing with three 100 ml portions of ammonium chloride solution, the combined organic phases were dried over magnesium sulphate. There were obtained 1.56 g (87%) of crude 1,2,3,4,9,10-hexahydro-2,3-dimethylene-1,4-epoxy-5-methoxyanthracene of melting point 145°-147° C. (from methanol).
Sources & evidence
- ORD record
- ord-6cb1befc5c8740429e824802f0c22352
- Source dataset
- uspto-grants-1981_11
- Patent number
- US04298535
Reaction notes
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