Thieno(2,3-b)pyridine-2-carbaldehyde → Thieno[2,3-b]pyridin-2-ylmethanol

Thieno[2,3-b]pyridine-2-carboxaldehyde (1.63 g) prepared according to J. Het. Chem. 355 (1974) was dissolved in ethanol (20 ml) and to the solution was added sodium borohydride (0.19 g). After 30 minutes the solution was evaporated to dryness and the residue extracted with methylene chloride (50 ml). The organic extract was washed with water (2×25 ml), the extract dried and then evaporated to obtain 2-hydroxymethylthieno[2,3-b]pyridine (1.40 g) as an amber oil. 'HNMR (CDCl3,60 MHz): 4.9 (s, 1H), 6.3 (s, 1H), 6.9 s, 1H), 7.1 (m, 1H), 7.8 (m, 1H), 8.4 (m, 1H). This product was dissolved in a solution of pyridine (2 ml) in methylene chloride (20 ml) and to the resulting solution was added methane sulfonyl chloride (1.14 g). Upon stirring overnight at room temperature, the solution was poured onto ice water (25 ml). The methylene chloride layer was separated, washed with water (2×10 ml) and then dried and evaporated. The residue was purified by chromatography on silica gel with a mixture of methylene chloride-ethyl acetate (9:1) as eluant to obtain the title compound (0.76 g; m.p. 47°-49° C.).

1. customAfter 30 minutes the solution was evaporated to dryness
2. extractionthe residue extracted with methylene chloride (50 ml)
3. extractionThe organic extract
4. washwas washed with water (2×25 ml)
5. customthe extract dried
6. customevaporated

ORD record

ord-a28c0fbcd66b4e7f8de5b0a2a09854e6

Source dataset

uspto-grants-1990_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04939140