Diethyl Ether → HCID 12985406, compound

Participants

Reaction Steps

The product of step 2 (845 mg, 3.09 mmoles) was dissolved in dichloromethane (10 mL), and dihydropyran (300 μL, 277 mg, 3.29 mmole) and p-toluenesulfonic acid monohydrate (3 crystals) were added. The solution was stirred at room temperature for 1.5 h. Diethyl ether (40 mL) was then added, and the solution was washed with saturated sodium bicarbonate (2×40 mL), dried over anhydrous sodium sulfate, and evaporated. Purification by column chromatography using ethyl acetate-hexanes (3:7) gave benzyl 3-[2-tetrahydropyranyloxy]-4-bromobutanoate (1.07 g, 97%) as a 1:1 mixture of diastereisomers. IR (neat): 3033, 1737 cm−1. Mass spectrum (CI, m/z): 357, 3539 (M+1, m+3). Calcd. for C16H21BrO4: C 53.75; H 5.88. Found: C 53.65; H 5.60.

Provenance & Evidence