Water → 2-Isopropylcyclopentane-1,3-dione

To a solution of TiCl4 (1.47 g, 7.77 mmol) and isobutyraldehyde (559 mg, 7.75 mmol) in DCM (16 ml) under N2 at −78° was added a solution of 1,2-bistrimethylsilyloxycyclobutene (1.97 g, 8.56 mmol) in DCM (16 ml) maintaining a temperature of less than −70°. After 30 min the reaction was poured into water, extracted into DCM, washed (H2O×2), dried (MgSO4) and the solution concentrated in vacuo to yield a clear oil. To this oil was added TFA (20 ml) and the solution heated at reflux for 24 h. The solution was concentrated in vacuo and the residue purified by chromatography (SiO2; 50:50 EtOAc/hexane) to give the title compound as an off-white solid (180 mg, 17%). δ H (d6-DMSO) 2.61 (1H, sept, J 7.0 Hz), 2.29 (4H, s), 1.04 (6H, d, J 7.0 Hz). m/z (ESI, 70V) 141 (MH+).

1. temperaturemaintaining a temperature of less than −70°
2. extractionextracted into DCM
3. washwashed (H2O×2)
4. dry with materialdried (MgSO4)
5. concentrationthe solution concentrated in vacuo
6. customto yield a clear oil
7. temperaturethe solution heated
8. temperatureat reflux for 24 h
9. concentrationThe solution was concentrated in vacuo
10. customthe residue purified by chromatography (SiO2; 50:50 EtOAc/hexane)

ORD record

ord-3ba4dac1bcb94c81a803300845731020

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06780874B2