Multi-step reaction with 11 steps
1: 91 percent / 70percent m-chloroperbenzoic acid, NaHCO3 / CH2Cl2 / Ambient temperature
2: 77 percent / Ti(iOPr)4 / 6 h / Ambient temperature
3: 49 percent / 1.) oxalyl chloride, DMSO, 2.) Et3N / CH2Cl2 / -50 °C / 1.) 15 min, 2.) 1 h
4: Et3N / tetrahydrofuran / 3 h / Ambient temperature
5: 2,6-lutidine, thionyl chloride / CH2Cl2 / 0.75 h / -40 °C
6: CH2Cl2 / Ambient temperature
7: 60 percent / 5.18 M NaOMe / methanol / 2.5 h / -40 °C
8: 87 percent / toluene / 3.5 h / 100 °C
9: 99 percent / 1.) oxalyl chloride, DMSO, 2.) Et3N / CH2Cl2 / -40 °C / 1.) 20 min, 2.) 1 h
10: sodium chlorite, sodium dihydrogen phosphate / tetrahydrofuran; various solvent(s); H2O / 3.5 h / Ambient temperature
11: 40 percent / phenyl dichlorophosphate, Et3N, 1.6 M ammonia/DMF / CH2Cl2 / 0.5 h / -25 °C
With
2,6-dimethylpyridine; titanium(IV) isopropylate; ammonium hydroxide; sodium chlorite; thionyl chloride; sodium dihydrogen phosphate; oxalyl dichloride; sodium methylate; sodium hydrogencarbonate; dimethyl sulfoxide; O-phenyl phosphorodichloridate; triethylamine; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene;