Butanal → 2-Propyl-1,3-cyclopentanedione

반응식

B(F)(F)F.CCOCC.[CH:10](=O)[CH2:11][CH2:12][CH3:13].C[Si](C)(C)[O:17][C:18]1[CH2:21][CH2:20][C:19]=1[O:22][Si](C)(C)C.C([O-])(O)=O.[Na+].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:11]([CH:10]1[C:19](=[O:22])[CH2:20][CH2:21][C:18]1=[O:17])[CH2:12][CH3:13]

참가 물질

반응물 5

HCID 261Butanal

HCID 6422Trifluoroacetic acid

HCID 8000Boron trifluoride etherate

HCID 516892Sodium Bicarbonate

HCID 27340341,2-Bis(trimethylsiloxy)cyclobutene

생성물 1

HCID 152539572-Propyl-1,3-cyclopentanedione

시약·촉매·용매 1

실험 절차

To a solution of BF3.OEt2 (1.30 g, 9.2 mmol) and butyraldehyde (0.40 g, 5.5 mmol) in DCM (5 ml) under N2 at −78° was added a solution of 1,2-bis trimethylsilyloxycyclobutene (1.4 g, 6.1 mmol) in DCM (3 ml) maintaining a temperature of less than −70°. After 2 h at −78° the solution was poured into saturated NaHCO3, extracted into EtOAc, washed (brine), dried (MgSO4) and the solution concentrated in vacuo to yield a clear liquid. To this liquid was added TFA (20 ml) and the solution heated at reflux for 24 h.