反应详情

Compound 43 was prepared by a procedure similar to that of Harada and co-workers (Harada, N. et al. Synth. Commun. 1995, 25, 767-772). To a vigorously stirring solution of octanoic acid (4.50 g, 31.2 mmol), sodium hydrogen carbonate (10.48 g, 124.8 mmol) and tetra-n-butylammonium hydrogen sulfate (1.06 g, 3.12 mmol) in water-dichloromethane (125 mL, 1:1 v/v) at 0° C. was added chloromethylchlorosulfate (5.15 g, 31.2 mmol) in dichloromethane (15 mL), and the reaction stirred at room temperature for a further 18 h. The mixture was diluted with dichloromethane (150 mL) and washed with brine (150 mL), dried over anhydrous magnesium sulfate and the solvent removed in vacuo. Purification by flash chromatography (hexane/ethyl acetate 9:1) afforded 43 as a yellow oil (5.28 g, 27.3 mmol, 88%). 1H NMR (400 MHz, CDCl3) δ 0.86-0.90 (3H, m, Me), 1.24-1.37 (8H, m, CH3(CH2)4), 1.60-1.71 (2H, m, CH2CH2COO), 2.36-2.40 (2H, m, CH2CH2COO), 5.71 (2H, s, CH2Cl).

1. customCompound 43 was prepared by a procedure similar to that of Harada and co-workers (Harada, N. et al. Synth. Commun. 1995, 25, 767-772)
2. washwashed with brine (150 mL)
3. dry with materialdried over anhydrous magnesium sulfate
4. customthe solvent removed in vacuo
5. customPurification by flash chromatography (hexane/ethyl acetate 9:1)