Tetrabutylammonium Fluoride → Methyl 4-(hydroxymethyl)-5-methylfuran-2-carboxylate

A stirred solution of 5-methyl-4-triisopropylsilanyloxymethyl-furan-2-carboxylic acid methyl ester (15) (5.2 g) in tetrahydrofuran (200 mL) was treated with tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran, 3.2 mL) and stirring continued for 16 hours. The reaction mixture was concentrated in vacuo and the residue taken up in ethyl acetate (350 mL) and washed with water (150 mL). The aqueous phase was re-extracted with ethyl acetate (2×100 mL). The combined extracts were dried, concentrated in vacuo and the residue was purified by flash chromatography eluting with ethyl acetate/pentane (1:1 by volume) to give compound 16 as a yellow oil.

1. concentrationThe reaction mixture was concentrated in vacuo
2. washwashed with water (150 mL)
3. extractionThe aqueous phase was re-extracted with ethyl acetate (2×100 mL)
4. customThe combined extracts were dried
5. concentrationconcentrated in vacuo
6. customthe residue was purified by flash chromatography
7. washeluting with ethyl acetate/pentane (1:1 by volume)

ORD record

ord-9a812479889d4cd9b75245cb9eb1f03d

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858644B2