Propanal → 2-Thiazolemethanol, -alpha--ethyl-

Temperature

0 °C

A 1.3 M solution of i-PrMgCl.LiCl (2.65 mL, 3.44 mmol) under an atmosphere of argon was cooled to −15° C. and treated with a solution of 2-bromothiazole (0.56 g, 3.4 mmol) in anhydrous THF (1 mL). The reaction mixture was then allowed to warm to 0° C. over 15 minutes. Propionaldehyde (0.25 mL, 3.4 mmol) was added and the solution was allowed to warm to room temperature over 18 hours. The solution was poured into saturated aqueous ammonium chloride (50 mL) containing crushed ice. The aqueous layer was extracted with EtOAc (50 mL) and washed with saturated aqueous sodium bicarbonate (100 mL). The aqueous layer was again extracted with EtOAc (50 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The material was purified by silica gel chromatography eluting with a gradient of 0-10% methanol in dichloromethane to afford 1-thiazol-2-yl-propan-1-ol.

1. temperatureto warm to room temperature over 18 hours
2. additioncontaining
3. customcrushed ice
4. extractionThe aqueous layer was extracted with EtOAc (50 mL)
5. washwashed with saturated aqueous sodium bicarbonate (100 mL)
6. extractionThe aqueous layer was again extracted with EtOAc (50 mL)
7. dry with materialThe combined organic layers were dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe material was purified by silica gel chromatography
11. washeluting with a gradient of 0-10% methanol in dichloromethane

ORD record

ord-0642320d8446462b95f4acc89f7bc0bc

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063065B2