Tetrahydrofuran → 7-oxabicyclo[2.2.1]hept-5-en-2-ylmethanol

A solution of methyl 7-oxanorborn-2-en-5-ylcarbonate (16.163 g, 105 mmol, see Example 1) in THF (75 ml) was added dropwise with stirring and under nitrogen to a suspension of lithium aluminium hydride (4.376 g, 115 mmol) in anhydrous THF (100 ml), in such a way that the solution boiled gently. The reaction mixture was subsequently stirred at room temperature for another 12 h and then quenched by cautiously adding an ice-water mixture. The organic phase was removed and the aqueous phase extracted with ethyl acetate (3×200 ml). The combined organic phases were washed with water (600 ml) and saturated sodium chloride solution (600 ml), dried over sodium sulphate and concentrated under reduced pressure.

1. customquenched
2. additionby cautiously adding an ice-water mixture
3. customThe organic phase was removed
4. extractionthe aqueous phase extracted with ethyl acetate (3×200 ml)
5. washThe combined organic phases were washed with water (600 ml) and saturated sodium chloride solution (600 ml)
6. dry with materialdried over sodium sulphate
7. concentrationconcentrated under reduced pressure

ORD record

ord-1eb356b06474435892b5420f5b881c26

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612008B2