2-(5-methylthiophen-2-yl)acetic Acid → 19498-70-5

A solution of 2-(5-methylthiophen-2-yl)acetic acid (200 mg, 1.280 mmol) in dry THF (10 mL) was carefully added over 2 min to solution of 1M LAH (2.56 mL, 2.56 mmol) 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-(5-methylthiophen-2-yl)ethanol (150 mg, 1.055 mmol, 82% yield) as clear viscous oil. 1H NMR (500 MHz, CDCl3) δ 6.67 (d, J=3.3 Hz, 1H), 6.64-6.57 (m, 1H), 3.85 (t, J=6.2 Hz, 2H), 3.02 (t, J=6.2 Hz, 2H), 2.47 (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-350c0897b0454fc98214bcd264615fdd

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193720B2