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-13f806e0f5e948a3b3fdd341312a613d

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858644B2