Multi-step reaction with 6 steps
1: 1.) lithium diisopropylamide / 1) THF, -78 deg C, 20 min; 2) THF, -78 deg C, 1 h
2: 73 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.75 h / -78 °C
3: diethyl ether / 1 h / Ambient temperature
4: 95 percent / oxalyl chloride, DMSO / CH2Cl2 / 1 h / -78 °C
5: 1.) hexamethyldisilazane, n-BuLi / 1) THF, -78 deg C, 45 min; 2) THF, hexane, -78 deg C, 2 h
6: 48 percent / PTSA / toluene / Heating
With
n-butyllithium; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,1,1,3,3,3-hexamethyl-disilazane; lithium diisopropyl amide;
In
diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo960221g