تفاعل #437722

معادلة التفاعل

methyl 3-nitro-4-hydroxybenzoate

N-Boc ethanolamine

PPh3

DIAD

→

methyl 3-nitro4-(2-aminoethoxy)benzoate

المردود 38.6%

المذيبات

CH2Cl2

THF

TFA

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture was then heated
2. 2
   درجة الحرارةunder reflux overnight
3. 3
   أخرىThe resulting mixture was evaporated
4. 4
   أخرىto give a gum
5. 5
   تركيزThe mixture was concentrated in vacuo
6. 6
   استخلاصThe mixture was extracted with CHCl3
7. 7
   غسيلwashed with brine
8. 8
   تجفيفdried over Na2SO4
9. 9
   أخرىThe solvent was evaporated in vacuo
10. 10
    أخرىto give the oily residue, which
11. 11
    أخرىwas purified by column chromatography on silica -gel with CHCl3

الإجراء التجريبي

To a stirred solution of methyl 3-nitro-4-hydroxybenzoate (1.98 g, 10.04 mmol), N-Boc ethanolamine (1.63 g, 10.11 mmol) and PPh3 (3.43 g, 13.08 mmol) in THF (40 mL) was added DIAD (2.57 mL, 13.05 mmol), and the reaction mixture was then heated under reflux overnight. The resulting mixture was evaporated to give a gum. The residual crude gum was dissolved in CH2Cl2 (30 mL) and TFA (30 mL), and the mixture was stirred for 1 hr at room temp. The mixture was concentrated in vacuo and made basic with sat. NaHCO3. The mixture was extracted with CHCl3, washed with brine, and dried over Na2SO4. The solvent was evaporated in vacuo to give the oily residue, which was purified by column chromatography on silica -gel with CHCl3 then CHCl3-MeOH (20:1, v/v) as eluent to give 930 mg (27% for 2 steps ) methyl 3-nitro4-(2-aminoethoxy)benzoate as gum. 1H-NMR (CDCl3) δ 3.16–3.19 (m, 1 H), 3.53–3.57 (m, 1 H), 3.90 and 3.94 (s, 3 H), 3.95–3.98 (m, 1 H), 4.21–4.24 (m, 1 H), 6.89–6.91 and 7.11–7.13 (m, 1 H), 8.03–8.19 and 8.21 (m, 1 H), 8.52 and 8.86 (m, 1 H).

المصدر