Diisobutylaluminum hydride → 3-(4-Iodopyrazol-1-yl)-2,2-dimethylpropan-1-ol

A cold (−20° C.) solution of 3-(4-Iodopyrazol-1-yl)-2,2-dimethylpropionic acid methyl ester (Compound 47F, 6.0 g, 19.48 mmol) in THF (80 mL) was treated with DIBAL (42.85 mL, 42.85 mmol, 1M solution in toluene) and allowed to warm to RT over a period of 2 h. The reaction mixture was treated with aq. ammonium hydroxide (20 mL) and the solids were filtered through celite. The filtrate was diluted with ethyl acetate (50 mL) and washed with brine (2×50 mL). The organic layer was dried over Na2SO4, filtered and concentrated to give 4.9 g (90%) as an oil which crystallized upon standing. 1H NMR (500 MHz, CDCl3) δ 7.50 (s, 1H), 7.41 (s, 1H), 4.0 (s, 2H), 3.17 (s, 3H), 0.9 (s, 6H).

1. filtrationthe solids were filtered through celite
2. additionThe filtrate was diluted with ethyl acetate (50 mL)
3. washwashed with brine (2×50 mL)
4. dry with materialThe organic layer was dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customto give 4.9 g (90%) as an oil which
8. customcrystallized

ORD record

ord-430cd4f409054bbda8a82a80d11ba53e

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133224B2