Hydrochloric Acid → HCID 21836085, compound

Participants

Reaction Steps

To a 250 mL two necked flask equipped with a condenser containing e-caprolactone (3,3 mL, 30 mmol) and anhydrous tetrahydrofuran (60 mL) under nitrogen atmosphere, was added at 0° C. dropwise propylmagnesium chloride (33 mL, 66 mmol, 2,2 eq., 2.0 M solution in diethyl ether). After addition, the reaction was stirred for 10 minutes at room temperature before heating to reflux for 2 hours. The reaction was monitored by thin layer chromatography. The reaction was cooled to 0° C. and saturated aqueous ammonium chloride (18 mL) was added followed, at room temperature, by hydrochloric acid (18 mL, 1 M aqueous). The organic phase was decanted and the aqueous phase extracted with dichloromethane (3×140 mL). The combined organic phases were washed with saturated aqueous sodium bicarbonate (100 mL) before drying over magnesium sulfate. Evaporation of the solvent gave the title compound (6,543 g, 96%) as a viscous yellow oil. 1H NMR (CDCl3, 400 MHz) d?(ppm): 3,64 (t, J=6,7 Hz, 2H); 1,59 (tt, J=6,7 Hz, J=6,7 Hz, 2H); 1,46-1,24 (m, 15H); 0,88 (t, J=7,2 Hz, 6Hd). 13C NMR (CDCl3, 129,9 MHz) d?(ppm): 68,5; 64,2; 42,0 (2C′); 39,8; 33,1; 26,8; 23,7; 17,1 (2C′); 14,5 (2C′). MS (IC+) m/z (%): 220,2 [M+18] (99); 202,2 (75); 203,3 [M+1] (30); 185,2 (100); 176,2 (60); 141,2 (25).

Provenance & Evidence