Morpholine → 4-(3-Butyn-1-yl)morpholine
Reaction equation
[CH2:1](OS(C)(=O)=O)[CH2:2][C:3]#[CH:4].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>CCOCC>[CH2:1]([N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[CH2:2][C:3]#[CH:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of methanesulfonic acid but-3-ynyl ester (10.1 g, 68 mmol) and morpholine (12.5 mL, 143 mmol) was heated to 100° C. for 1 h. The mixture was diluted with Et2O (50 mL) and filtered. The solid residue was discarded, and the mother liquor extracted with 3N HCl. The aqueous layer was basified with NaOH, and back-extracted into EtOAc. Drying (Na2SO4), concentration, and distillation (short-path, b.p.=130° C. at ˜5 mm Hg) game the title compound as a colorless oil. 1H NMR (CDCl3) δ 3.72 (t, 4H), 2.60 (t, 2H), 2.48 (t, 4H), 2.39 (td, 2H), 2.00 (t, 1H).