반응 #1669395

반응 방정식

NH4Cl

5-bromo-pentanol

Et3N

TBDPSCl

→

TBDPSOH

수율 155.3%

용매

CH2Cl2

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   추출The aqueous layer was extracted with EtOAc (3×100 mL)
3. 3
   건조the organic layers were dried (Na2SO4)
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타The crude product was chromatographed
7. 7
   세척(SiO2, 5×20 cm, 0-20% EtOAc/hexanes, gradient elution)

실험 절차

A solution of 5-bromo-pentanol (0.9889 g, 5.9 mmol, 1 eq) in anhydrous CH2Cl2 (20 mL) under N2 at 25° C. was treated with anhydrous Et3N (1.0 mL, 7.2 mmol, 1.2 eq), TBDPSCl (1.7 mL, 6.5 mmol, 1.1 eq) and DMAP (0.23 g, 1.9 mmol, 0.3 eq). The reaction mixture was stirred for 2 h before an aqueous solution of saturated NH4Cl (100 mL) was added. The aqueous layer was extracted with EtOAc (3×100 mL) and the organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was chromatographed (SiO2, 5×20 cm, 0-20% EtOAc/hexanes, gradient elution) to afford TBDPSOH (2.35 g, 98%) as a clear oil; 1H NMR (CDCl3, 400 MHz) δ 7.66-7.60 (m, 4H), 7.44-7.33 (m, 6H), 3.64 (t, 2H, J=6.1 Hz), 3.37 (t, 2H, J=6.9 Hz), 1.82 (p, 2H, J=7.3 Hz), 1.59-1.45 (m, 4H), 1.03 (s, 9H); 13C NMR (CDCl3, 100 MHz) δ 135.6, 129.6, 127.6, 127.5, 63.5, 33.9, 32.5, 31.6, 26.8, 24.5, 19.2; IR (film) υmax 3069, 2930, 2856, 2359, 1470, 1427, 1389, 1106, 822, 738, 700 cm−1; FABHRMS (NBA-CsI) m/z 537.0235 (C21)H29OSiBr+Cs+ requires 537.0225).

출처