Реакция #502125

Уравнение реакции

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

2-bromoethanol

ether hexane

→

title compound

Выход 84.1%

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

Выход 84.1%

Растворители

DMF

CH2Cl2

Условия реакции

Обработка

1. 1
   ДругоеThe excess 2-bromoethanol and DMF were evaporated under vacuum at 60° C
2. 2
   ДругоеThe resulted crude material
3. 3
   Промывкаwashed with water (400 mL), saturated NaHCO3 (100mL), 3N HCl (100 mL), brine
4. 4
   Сушкаdried over Na2SO4
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated

Методика

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)+.

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