Water → [2-(4-Methoxyphenyl)-1,3-thiazol-4-yl]methanol

Temperature

60 °C

To an ice-cold suspension of LAH (0.08 g, 2.07 mmol) in 10 ml of anhydrous THF was added a solution of 2-(4-Methoxy-phenyl)-thiazole-4-carboxylic acid ethyl ester (0.26 g, 0.98 mmol) in 5 ml of THF. The reaction mixture was heated up to 60° C. for 1 h. After the completion of the reaction mixture (TLC monitoring), the reaction mixture was cooled to 0° C., water (2.0 ml) was added followed by the addition of 15% NaOH solution (2 mL) and finally 4 ml of water. The resulting solution was filtered through celite bed and concentrated under reduced pressure; water (25 mL) was added and extracted with ethyl acetate (3×50 mL). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated to give the desired product (0.14 g, 64%).

1. temperatureAfter the completion of the reaction mixture (TLC monitoring), the reaction mixture was cooled to 0° C.
2. filtrationThe resulting solution was filtered through celite bed
3. concentrationconcentrated under reduced pressure
4. additionwater (25 mL) was added
5. extractionextracted with ethyl acetate (3×50 mL)
6. washThe combined organics was washed with water, brine
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-8657095d0c8c4d19b489d9c1b6e26850

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088791B2