반응 #1244277

반응 방정식

water

23

2-Azidopropane-1,3-diol

(trimethoxymethyl)benzene

→

monoacylated product 27

수율 93.0%

2-Azido-3-hydroxypropyl benzoate

수율 93.0%

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   농축concentrated in vacuo
2. 2
   기타Purification of the residue by silica gel flash chromatography

실험 절차

Neat 23 (1.48 g, 12.65 mmol) was dissolved in CH2Cl2 (127 mL) and treated with a catalytic amount of p-toluene sulfonic acid monohydrate (0.048 g, 20 μmol) and (trimethoxymethyl)benzene (3.26 mL, 18.98 mmol) in CH2Cl2 at room temperature for 1 hr. After the formation of the orthoester was complete, a stoichiometric amount of water (340 μL, 18.98 mmol) was added to the mixture. The mixture was then stirred for 40 min and concentrated in vacuo. Purification of the residue by silica gel flash chromatography using 25% EtOAc/hexanes gave 2.6 g of monoacylated product 27 (93% yield) as a clear, colorless oil. 1H NMR (CDCl3, 400 MHz) δ: 8.03-8.06 (m, 2H), 7.58 (tt, J=1.6, 2.0, 1.6 1H), 7.43-7.47 (m, 2H), 4.54 (dd, J=4.4, 12.0 Hz, 1H), 4.46 (dd, J=6.8, 12.0 Hz, 1H), 3.85-3.91 (m, 1H), 3.80 (dd, J=4.8, 11.6 Hz, 1H), 3.73 (dd, J=6.0, 11.6 Hz, 1H).

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