Red-Al → HCID 70487303, compound

Red-al [70% solution of sodium bis(2-methoxyethyl)- aluminum hydride in benzene, 1.2 g., 1.1 ml., 5.86 mmoles]was cooled under nitrogen in an ice bath. A solution of ethyl 2-(4-pyridylmethylthio)propionate in 10 ml. of dry tetrahydrofuran was added dropwise over 10 minutes. The mixture was then heated and gently refluxed for 1 hour and then stirred at room temperature for approximately 16 hours. The reaction mixture was poured into 40 ml. of ice cold 1N HCl and salts removed by filtration. The filtrate was made basic with sodium bicarbonate and the product extracted into ethyl acetate (four times with 50 ml. aliquots). The combined ethyl acetate extracts were dried (by wash with saturated sodium chloride and then over anhydrous sodium sulfate) and concentrated to yield 4-(1-hydroxy-2-propylthiomethyl)pyridine (oil; approximately 200 mg.; pnmr/CDCl3 /TMS/delta: 8.6 (d, 3H), 7.2 (s, broad, 1H), 6.3 (m, 5H), 2.7 (d, 2H), 1.5 (d, 2H); m/e calcd: 183; found: 183, 152, 118, 92, 65; ir (film): 3.1, 6.25, 7.1, 9.25, 12.25μ). To further purify the product, it was taken up in chloroform, treated with activated carbon and concentrated to an oil (194 mg.).

1. temperatureThe mixture was then heated
2. temperaturegently refluxed for 1 hour
3. additionThe reaction mixture was poured into 40 ml
4. customof ice cold 1N HCl and salts removed by filtration
5. extractionthe product extracted into ethyl acetate (four times with 50 ml. aliquots)
6. dry with materialThe combined ethyl acetate extracts were dried (
7. washby wash with saturated sodium chloride
8. concentrationover anhydrous sodium sulfate) and concentrated

ORD record

ord-3a8220c7adb94909b77a54f952668755

Source dataset

uspto-grants-1985_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04535084