Multi-step reaction with 10 steps
1: 1.) copper acetate monohydrate, oxygen / 1.) methanol, room temp., 10 min
2: 1.) 1 M aq. Na2S2O4 (pH 7.0), 2.) Na2S2O4 / 1.) 3-pentanone, 15 min, 2.) reflux, 105 min
3: K2CO3 / various solvent(s) / 1.5 h / Heating
4: various solvent(s) / 41 h
5: 83 percent / barium hydroxide octahydrate / dimethylformamide / 32 h / Ambient temperature
6: 96 percent / H2 / 5percent Pd/C / methanol / 42 h / 2585.7 Torr
7: 100 percent / K2CO3 / dimethylformamide / 10.5 h
8: 61 percent / various solvent(s) / 2.5 h / Heating
9: 84 percent / anhydrous K2CO3 / acetonitrile / 24 h
10: 33 percent / 1percent aq. osmium tetraoxide, NaIO4 / diethyl ether / 16 h / Ambient temperature
With
sodium periodate; osmium(VIII) oxide; sodium dithionite; barium hydroxide octahydrate; hydrogen; oxygen; copper (I) acetate; potassium carbonate;
palladium on activated charcoal;
In
methanol; diethyl ether; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00133a034