Triethylamine → methanesulfonic acid 5-benzyloxy-4-oxo-4H-pyran-2-ylmethyl ester

Participants

Reaction Steps

To an ice/salt cooled suspension of 5-benzyloxy-2-hydroxymethyl-pyran-4-one (30.0 g, 0.129 mol) in dichloromethane (500 mL) were added, successively, triethylamine (21.0 mL, 0.151 mol) and a solution of methanesulfonyl chloride (8.3 mL, 0.129 mol) in 10 mL of dichloromethane. The progress of the reaction was monitored by TLC (CH2Cl2/MeOH, 10/1, v/v), and by HPLC Method 1 as described above. An additional methanesulfonyl chloride (0.5 mL, 7.70 mmol) and triethylamine (2.0 mL, 14.2 mmol) were added to the solution after 50 min. Again, an additional methanesulfonyl chloride (1.0 mL, 15.4 mmol) and triethylamine (2 mL, 14.2 mmol) were added an hour later. The reaction was quenched with 150 mL of brine. The organic phase was separated and collected, dried over sodium sulfate and concentrated in vacuo to give an oil. The oil was diluted with 200 mL of hexanes and a precipitate was formed. The solid was collected by suction filtration, and dried in a vacuum oven to give methanesulfonic acid 5-benzyloxy-4-oxo-4H-pyran-2-ylmethyl ester (39 g, 85% yield). HPLC purity (peak area percent) is 82.1% at λ=280 nm using HPLC Method 1 as described above. 1H NMR (400 MHz, DMSO-D6) δ (ppm): 8.32 (m, 1H), 7.43-7.37 (m, 5H), 6.62 (m, 1H), 5.18 (m, 2H, OCH2), 4.98 (m, 2H, OCH2), 3.36 (m, 3H, SCH3).

Provenance & Evidence