Water → HCID 14382036, compound

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%). δH (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-f2e62fe7b3e14a569371d00e27330a2d

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610700B2