Triethylamine → HCID 76764491, compound

Participants

Reaction Steps

A solution of hydroxyester 75 (100 mg, 0.342 mmol, 1.00 equiv) and triethylamine (166 μL, 1.20 mmol, 3.50 equiv) in CH2Cl2 (14 mL) was added via syringe pump over 4 h to a solution of 2,4,6-trichlorobenzoyl chloride (80 μL, 0.51 mmol, 1.5 equiv) and N,N-dimethylaminopyridine (DMAP) (46 mg, 0.38 mmol, 1.1 equiv) in CH2Cl2 (3.4 mL). The solution was then allowed to stir for 1 h after complete addition after which time it was quenched with H2O (10 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (2×10 mL). The organic phases were combined, dried over Na2SO4, and the solvent was removed via rotary evaporation to yield a red solid which was purified by silica gel column chromatography (CH2Cl2) to yield S10 (47 mg, 50%) as a pale yellow oil. Rf=0.79 (60:38:2 Hex:EtOAc:HOAc); 1H NMR (500 MHz, CDCl3) δ 7.37 (m, 5H, ArH), 5.25 (s, 2H, ArCH2), 5.09 (m, 1H, vinyl H), 3.61 (d, 1H, J=16.4 Hz, C(O)CH2), 3.36 (d, 1H, J=16.4 Hz, C(O)CH2), 2.79 (m, 2H, CHCH2), 1.70 (d, 3H, J=0.8 Hz, CH3), 1.60 (d, 3H, J=0.8 Hz, CH3); 13C NMR (100 MHz, CDCl3) δ 169.21, 165.84, 138.67, 134.67, 128.68, 128.38, 114.24, 76.28, 67.84, 45.56, 33.43, 25.87, 17.99; IR (neat film) 2966 (m), 2914 (m), 1842 (s), 1737 (s), 1452 (m) 962 (m) cm−1; HRMS (EI) m/z calcd for C16H18O4 (M+) 274.120509; observed 274.120646; [α]D=+1.2° (c 2.92, CHCl3).

Provenance & Evidence