Boron trifluoride etherate → 5-Hydroxy-2-methyl-5-(2-trimethylsilylfuran-4-yl)-2-pentenal

To a stirred solution of 5-trimethylsilyl-3-furaldehyde (0.382 g., 2.27 mmol) in dry methylene chloride (15 ml) at -50° under argon was added dropwise boron trifloride etherate (0.28 ml, 2.3 mmol). This addition was followed by the dropwise addition of 2-methyl-l-trimethylsilyloxy-1,3-butadiene (0.356 g., 2.3 mmol). The solution was stirred at -50° to -60° for 18 hours, quenched by the addition of several ml saturated sodium bicarbonate solution, warmed to room temperature and poured into methylene chloride. The organic portion was washed once with saturated bicarbonate solution, once with water, once with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a yellow oil which consisted of several components by TLC. The mixture was applied to a chromatography column (silica) and eluted with 30% ethyl acetate/hexane. Eluted last was the desired alcohol, which was concentrated to give a yellow gum.

1. additionThis addition
2. customquenched by the addition of several ml saturated sodium bicarbonate solution
3. additionpoured into methylene chloride
4. washThe organic portion was washed once with saturated bicarbonate solution, once with water, once with saturated sodium chloride solution
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customto give a yellow oil which
9. washeluted with 30% ethyl acetate/hexane
10. washEluted last
11. concentrationwas concentrated
12. customto give a yellow gum

ORD record

ord-ecddb45f3d1442c4bcd38b116424b09b

Source dataset

uspto-grants-1993_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05258400