Multi-step reaction with 8 steps
1: HCl (g)
2: 1.) triethylamine, 2.) KOH / 1.) CHCl3, 0 deg C, 16 h, 2.) propylene glycol, reflux, 15 min
3: 88 percent / triethylamine, N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 1.) 0 deg C, 2 h, 2.) RT, overnight
4: 92 percent / HCl / ethanol; H2O / 3 h / Heating
5: 1.) triethylamine, molecular sieve (4A) / 1.) acetonitrile, 0 deg C, 1 h, 2.) a) acetonitrile, 0 deg C, 1 h, b) acetonitrile, RT, overnight
6: pyridine / 1 h / Ambient temperature
7: 68 percent / CHCl3 / Ambient temperature
8: 77 percent / POCl3, triethylamine / CH2Cl2 / 1.5 h / -40 °C
With
hydrogenchloride; potassium hydroxide; 4 A molecular sieve; triethylamine; dicyclohexyl-carbodiimide; trichlorophosphate;
In
pyridine; ethanol; dichloromethane; chloroform; water;
DOI:10.1021/jo00217a023