Hexachloroacetone → HCID 68634052, compound

Participants

Reaction Conditions

Reaction Steps

Compound 10 (813 mg, 1.88 mmol) and triphenylphosphine (995 mg, 3.76 mmol) were dissolved in CH2Cl2, and then at −78° C., hexachloroacetone (0.57 mL, 3.76 mmol) was added dropwise to the solution. The reaction temperature was raised to 0° C., and the progress of the reaction was monitored by TLC which indicated that it was over in 40 min Solvent was removed at room temperature and the crude product was chromatographed (SiO2, gradient, hexane/EtOAc 10:1 to 8:1) to give 834 mg (1.85 mmol, 98%) of 36 as a clear colorless oil. Rf 0.89 (hexane/EtOAc 1:1); 1H NMR (400 MHz, CDCl3) 7.68 (m, 4H, H-2 of phenyl), 7.45-7.35 (m, 6H, H-3 and H-4 of phenyl), 3.81 (t, 2H, J=5.4 Hz, CH2CH2OSi), 3.74 (t, 2H, J=6.0 Hz, CH2CH2Cl), 3.67-3.59 (m, 12H, ClCH2CH2(OCH2CH2)2OCH2CH2OSi), 1.05 (s, 9H, C(CH3)3); MS (ESI) Calcd for C24H35ClO4SiNa (M+Na+): 473.2. Found: 473.2.

Provenance & Evidence