4-Toluenesulfonyl chloride → HCID 86599740, compound

Participants

Reaction Steps

To a solution of 10 (1.06 g, 2.46 mmol) in 30 mL of CH2Cl2 was added triethylamine (0.62 mL, 4.45 mmol). 4-Toluenesulfonyl chloride (TsCl, 567 mg, 2.97 mmol) was added to this solution in one portion at 0° C., and the mixture was stirred at under Ar for 24 h allowing it to warm to room temperature slowly. The reaction was quenched by pouring into a mixture of water (100 mL) and chloroform (70 mL), separated organic layer, and the aqueous layer was further extracted with chloroform (100 mL). The combined organic layers were dried over sodium sulfate (Na2SO4) and concentrated. The crude product was chromatographed (SiO2, gradient, hexane/EtOAc 5:1 to 2:1) to give 1.08 g (1.85 mmol, 75%) of 11 as a clear colorless oil. Rf 0.65 (hexane/EtOAc 1:1); 1H NMR (400 MHz, CDCl3) 7.79 (d, 2H, J=8.3 Hz, H-2 of tosyl), 7.68 (m, 4H, H-2 of phenyl), 7.44-7.35 (m, 6H, H-3 and H-4 of phenyl), 7.32 (d, 2H, J=8.7 Hz, H-3 of tosyl), 4.14 (t, 2H, J=4.9 Hz, TsOCH2CH2), 3.80 (t, 2H, J=5.3 Hz, CH2OSi), 3.66 (t, 2H, J=4.9 Hz, TsOCH2CH2), 3.64-3.54 (m, 10H, (OCH2CH2)2OCH2CH2OSi), 2.43 (s, 3H, CH3 of tosyl), 1.04 (s, 9H, C(CH3)3); MS (ESI) Calcd for C31H42O7SSiNa (M+Na+): 609.2. Found: 609.2.

Provenance & Evidence