반응 #552810

반응 방정식

sodium hydride

1,3-propanediol

benzyl bromide

→

3-benzyloxypropan-1-ol

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture is stirred at room temperature for 62 hours
2. 2
   기타The solvent is evaporated
3. 3
   기타the residue purified by flash chromatography over silica gel using 1:4 ethylacetate/hexane as eluent

실험 절차

To a suspension of sodium hydride (5.6 g, 0.14 mole) in tetrahydrofuran (350 ml) is added 1,3-propanediol (15 ml, 0.21 mol). The gummy suspension is stirred at room temperature for 0.5 hour and tetra n-butylammonium iodide (0.54 g) is added followed by benzyl bromide (16.6 ml, 0.14 mole). The mixture is stirred at room temperature for 62 hours. The solvent is evaporated and the residue purified by flash chromatography over silica gel using 1:4 ethylacetate/hexane as eluent to obtain 3-benzyloxypropan-1-ol as a clear oil; 1H NMR (CDCl3): δ7.3 (m, 5H), 4.5 (s,2H), 3.78 (t,8 Hz,2H), 3.65 (t,8 Hz,2H), 1.87 (quintet,8 Hz,2H).

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