反応 #502125

反応方程式

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

2-bromoethanol

ether hexane

→

title compound

収率 84.1%

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

収率 84.1%

溶媒

DMF

CH2Cl2

反応条件

後処理

1. 1
   その他The excess 2-bromoethanol and DMF were evaporated under vacuum at 60° C
2. 2
   その他The resulted crude material
3. 3
   洗浄washed with water (400 mL), saturated NaHCO3 (100mL), 3N HCl (100 mL), brine
4. 4
   乾燥dried over Na2SO4
5. 5
   ろ過filtered
6. 6
   濃縮concentrated

実験手順

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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