Acetophenone → HCID 15880897, compound

To a solution of acetophenone (1.21 g, 10.07 mmol) in dry toluene (5 mL) was added LiHMDS (11.0 mL, 1.0 M in THF, 11.0 mmol) via syringe at 0° C. under argon. After 5 min, isobutyryl chloride (1.073 g, 10.07 mmol) was added in one portion via syringe. The ice bath was removed and AcOH (2 mL), EtOH (50 mL) and THF (5 mL) were added to form a homogeneous mixture. Hydrazine hydrate (2 mL, 10.07 mmol) was added and the reaction was refluxed for 2 h. After cooled to room temperature, the reaction was concentrated and extracted with EtOAc, washed with brine, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as colorless oil (0.70 g). LCMS m/z=187.3 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.33 (d, J=6.82 Hz, 6H), 2.94-3.13 (m, 1H), 6.38 (s, 1H), 7.17-7.45 (m, 5H), 10.14 (bs, 1H).

1. customThe ice bath was removed
2. additionAcOH (2 mL), EtOH (50 mL) and THF (5 mL) were added
3. customto form a homogeneous mixture
4. temperaturethe reaction was refluxed for 2 h
5. concentrationthe reaction was concentrated
6. extractionextracted with EtOAc
7. washwashed with brine
8. dry with materialdried over MgSO4
9. concentrationconcentrated
10. customThe residue was purified by silica gel column chromatography

ORD record

ord-ad870c90a4484a58929c94fcfcb8f57b

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012478B2