Tetrabutylammonium Fluoride → (4-Hydroxymethyl-5-methyl-furan-2-yl)-acetic acid ethyl ester

A solution of (5-methyl-4-triisopropylsilanyloxymethyl-furan-2-yl)-acetic acid ethyl ester (29) (0.5 g) in tetrahydrofuran (3.0 mL) was cooled to 0° C. with stirring and treated with tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran, 2.82 mL) under argon. After 30 minutes, the resulting solution was concentrated in-vacuo and partitioned between water (30 mL) and ethyl acetate (4×25 mL). The combined organic extracts were washed with brine (50 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography eluting with diethyl ether/petroleum ether (1:1 by volume) to give compound 30 as a clear oil (188 mg). LC/MS System A: Rt=2.34 mins.

1. concentrationthe resulting solution was concentrated in-vacuo
2. custompartitioned between water (30 mL) and ethyl acetate (4×25 mL)
3. washThe combined organic extracts were washed with brine (50 mL)
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by flash chromatography
8. washeluting with diethyl ether/petroleum ether (1:1 by volume)

ORD record

ord-19908e3c82524e45aa407567b39a0d94

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07528157B2