تفاعل #502125

معادلة التفاعل

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

2-bromoethanol

ether hexane

→

title compound

المردود 84.1%

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

المردود 84.1%

المذيبات

DMF

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىThe excess 2-bromoethanol and DMF were evaporated under vacuum at 60° C
2. 2
   أخرىThe resulted crude material
3. 3
   غسيلwashed with water (400 mL), saturated NaHCO3 (100mL), 3N HCl (100 mL), brine
4. 4
   تجفيفdried over Na2SO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated

الإجراء التجريبي

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 (100mL), 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)+.

المصدر