반응 #1449991

반응 방정식

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid sodium salt

2-bromoethanol

ether hexane

→

title compound

수율 84.1%

2-Hydroxyethyl(2S)-2-(6-methoxy(2-naphthyl))-propanoate

수율 84.1%

용매

DMF

CH2Cl2

반응 조건

후처리

1. 1
   기타The excess 2-bromoethanol and DMF were evaporated under vacuum at 60° C
2. 2
   기타The resulted crude material
3. 3
   세척washed with water (400 mL), saturated NaHCO3 (100 mL), 3N HCl (100 mL), brine
4. 4
   건조dried over Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated

실험 절차

A solution of (2S)-2-(6-methoxy(2-naphthyl))propanoic acid sodium salt (10.9 g, 43.2 mmol) and 2-bromoethanol (27.11 g, 0.22 mol) in DMF (150 mL) was heated to 80° C. for 3.5 hours. The excess 2-bromoethanol and DMF were evaporated under vacuum at 60° C. The resulted crude material was dissolved in CH2Cl2 (400 mL) and washed with water (400 mL), saturated NaHCO3 (100 mL), 3N HCl (100 mL), brine and dried over Na2SO4, filtered and concentrated. Trituration of the residue with ether/hexane gave the title compound as a white solid (9.97 g, 84% yield). m.p. 72-73° C. 1H NMR (300 MHz, CDCl3) δ 8.0-7.68 (m, 3H), 7.66-7.61 (m, 1H), 7.16-7.1 (m, 2H), 4.25-4.15 (m, 2H), 3.93 (s, 3H), 3.92 (q, J=7.2 Hz, 1H), 3.75-3.70 (m, 2H), 1.78 (br. t, 1H), 1.59 (d, J=7.2 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 174.7, 157.3, 135.2, 133.4, 129.9, 128.6, 126.9, 125.8, 125.6, 118.6, 105.3, 65.9, 60.3, 54.8, 45.0, 18.2. MS (API) m/z 275 (M+NH4)+.

출처