Lithium hydroxide, monohydrate → 69193-39-1

Temperature

0 °C

To a mixture of 3-(5-chloro-thiophen-2-yl)-(E)-acrylic acid methyl ester (0.60 g, 2.96 mmol) in 15 mL of 1:1:1 THF/MeOH/H2O at 0° C. is added lithium hydroxide monohydrate (0.62 g, 14.7 mmol). The mixture is stirred at 0° C. for 1 h, then at room temperature for 1 h and concentrated in vacuo. The residue is diluted with EtOAc and washed with 1N HCl. The aqueous layer is extracted with EtOAc and the combined organics are washed with water (2×), dried, filtered and concentrated to provide the title compound (0.54 g, 2.86 mmol) as a white solid. The crude material can be used in the subsequent step without further purification. 1H NMR (CDCl3, 300 MHz) δ7.65 (d, 1H), 7.05 (d, 1H), 6.90 (d, 1H), 6.10 (d, 1H).

1. waitat room temperature for 1 h
2. concentrationconcentrated in vacuo
3. additionThe residue is diluted with EtOAc
4. washwashed with 1N HCl
5. extractionThe aqueous layer is extracted with EtOAc
6. washthe combined organics are washed with water (2×)
7. customdried
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-3e3ce469d6df4ed887b7bb4640b3e2a8

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612075B2