Multi-step reaction with 8 steps
1: 85 percent / t-BuOK / 2-methyl-propan-2-ol; 1,2-dimethoxy-ethane / 3 h / Ambient temperature
2: 97 percent / NaOH / ethanol; H2O / 5 h / Heating
3: oxalyl chloride / CH2Cl2 / 0 deg c, 4 h, then rt., 1 h
4: Et3N / CH2Cl2 / 16 h / Ambient temperature
5: 1.) LDA, diphenyl phosphorochloridate; 2.) NaN3 / 1.) THF/heptane/ethylbenzene, rt., 24 h; 2.) THF/heptane/ethylbenzene, rt., 3 d
6: 80 percent / acetonitrile / 16 h / Ambient temperature
7: 95 percent / 6N HCl / tetrahydrofuran / 4 h / Ambient temperature
8: 76 percent / tetrahydrofuran / 16 h / Ambient temperature
With
hydrogenchloride; sodium hydroxide; sodium azide; oxalyl dichloride; potassium tert-butylate; triethylamine; chlorophosphoric acid diphenyl ester; lithium diisopropyl amide;
In
tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; acetonitrile; tert-butyl alcohol;
DOI:10.1002/hlca.19970800515