Multi-step reaction with 10 steps
1: 92 percent / Et3N, DMAP / CH2Cl2 / 5 h
2: NaH, DMPU / tetrahydrofuran / -10 deg C, 45 min, -10 deg C to rt, 4 h
3: 84 percent / NaBH4 / tetrahydrofuran; bis-(2-methoxy-ethyl) ether / 0.33 h / -78 - -45 °C
4: 89 percent / Ph3P, NBS / tetrahydrofuran / 0.25 h / 5 °C
5: 87 percent / 1.) Zn, 1,2-dibromoethane, 2.) (Ph3P)4Pd / tetrahydrofuran / 1.) -5 deg C, 4.75 h, 2.) 60 deg C, 17 h
6: 95 percent / AcOH, Bu4NF / tetrahydrofuran / 1 h
7: 97 percent / Ph3P, NBS / tetrahydrofuran / 10 deg C to rt
8: 83 percent / 1.) Zn, 1,2-dibromoethane, 2.) (Ph3P)4Pd / tetrahydrofuran
9: 83 percent / AcOH, Bu4NF / tetrahydrofuran / 1 h
10: 96 percent / Ph3P, NBS / tetrahydrofuran / 10 deg C to rt
With
dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride; sodium hydride; acetic acid; ethylene dibromide; triethylamine; triphenylphosphine; zinc;
In
tetrahydrofuran; dichloromethane; diethylene glycol dimethyl ether;
DOI:10.1021/jo970596h