Sodium hydride → HCID 19874747, compound

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Reaction Steps

To a suspension of sodium hydride (0.24 g, 6 mmol) in dioxane (20 ml) is added 3-benzyloxypropan-1-ol (1.0, 6 mmol) and the mixture is allowed to stir at room temperature for 1 hour. t-Butyl bromoacetate (1.05 g, 6.5 mmol) is added slowly and the mixture is allowed to stir for 18 hours. The solvent is evaporated and saturated ammonium chloride (20 ml) is added. The mixture is extracted with methylene chloride (3×20 ml) and the combined organic extracts are dried, filtered and evaporated. Purification by flash column chromatography on silica gel using ethyl acetate/hexane (1:4) as eluent yields 3-benzyloxypropyl-2-[(3-benzyloxypropyl)oxy]-acetate; 1H NMR (CDCl3): δ7.3 (m, 10H), 4.48 (q,4H), 4.27 (t,8 Hz,2H), 4.0 (s,2H), 3.56 (m,6H), 1.92 (m,2H).

Provenance & Evidence