Multi-step reaction with 4 steps
1: 1) BuLi, propyl nitrate, 2) aqueous HCl / in THF/hexane, 1) 0 deg C, 45 min., 2) o deg C, 2h, 3) RT, 2h
2: 1) KOH, 2) HOAc / methanol, 1) 1h -10 deg C, 7h 0 deg C, 2) RT, 2h
3: 80 percent / triethylamine, methanesulfonyl chloride / CH2Cl2 / 1) -78 deg C, 5 min., 2) 0 deg C, 3h
4: 100 percent / KF / 1,2-dimethoxy-ethane / 1) 30 min. RT, 2) 3h, 50-60 deg C
With
hydrogenchloride; potassium fluoride; potassium hydroxide; n-butyllithium; propyl nitrate; acetic acid; methanesulfonyl chloride; triethylamine;
In
1,2-dimethoxyethane; dichloromethane;
DOI:10.1021/jo01303a005