Multi-step reaction with 9 steps
1: 86 percent / H2 / PtO2 / ethyl acetate / 2327.2 Torr
2: KH, MeOH / diethyl ether / 4 h / Heating
3: oxalyl chloride, DMF / acetonitrile / 1.) 0 deg C, 15 min, 2.) -22 deg C, 15 min
4: NH3 / acetonitrile; tetrahydrofuran / 1 h / -76 - 20 °C
5: 99 percent / H2 / 10percent Pd/C / ethyl acetate / 2585.7 Torr
6: 18 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent) / tetrahydrofuran / 24 h
7: KOH / H2O; tetrahydrofuran / 0.5 h
8: 63 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / benzene / 12 h / Heating
9: O2 / Irradiation
With
Lawessons reagent; methanol; potassium hydroxide; oxalyl dichloride; ammonia; hydrogen; oxygen; potassium hydride; N,N-dimethyl-formamide; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
platinum(IV) oxide; palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; water; ethyl acetate; acetonitrile; benzene;
DOI:10.1021/jo00269a024