5-Thiazoleacetic acid, 2,4-dimethyl- → 2-(2,4-Dimethylthiazol-5-yl)ethanol

A solution of 2-(2,4-dimethylthiazol-5-yl)acetic acid (230 mg, 1.343 mmol) in dry THF (10 mL) was carefully added over 2 min to solution of 2M LAH (1.343 mL, 2.69 mmol) in dry THF (10 mL) at 0° C. The reaction mixture was allowed to warm to rt and was stirred for 6 h. The reaction was quenched with 0.2 mL of water (stir for 10 min), 0.2 mL of 15% NaOH/water (stir for 10 min), and then 0.4 mL of water. After stirring for 18 h, the mixture was filtered through celite. The filtrate was concentrated in vacuum. The residue was dried under high vacuum for 16 h to afford 2-(2,4-dimethylthiazol-5-yl)ethanol (180 mg, 1.145 mmol, 85% yield) as a clear viscous oil. 1H NMR (500 MHz, CDCl3) δ 3.83 (t, J=6.3 Hz, 2H), 2.97 (t, J=6.3 Hz, 2H), 2.64 (s, 3H), 2.35 (s, 3H).

1. customThe reaction was quenched with 0.2 mL of water (stir for 10 min), 0.2 mL of 15% NaOH/water (stir for 10 min)
2. stirringAfter stirring for 18 h
3. filtrationthe mixture was filtered through celite
4. concentrationThe filtrate was concentrated in vacuum
5. customThe residue was dried under high vacuum for 16 h

ORD record

ord-026878e327904ced9fd99b0f3b02ac36

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193720B2