4-Benzyloxy-1,3-butanediol synthesis

Yield:71998-70-4 69%

Reaction Conditions:

with copper(l) iodide;methyllithium in diethyl ether at -40 - 0; for 3 h;Inert atmosphere;regioselective reaction;

Steps:

To a stirred suspension of CuI (14.7 g, 74.2 mmol) in anhydrous Et₂O (147 mL) at 0 °C was added slowly MeLi (92.7 mL, 0.148 mmol, 1.6 M in Et₂O) under an N₂ atm, and the resulting solution was stirred for 15 min at 0 °C. Epoxy alcohol 16 (4.8 g, 24.7 mmol) in anhydrous Et₂O (20 mL) was then added dropwise at -40 °C. Once the addition was complete, the mixture was stirred at 0 °C for 3 h. The reaction was quenched by the careful addition of sat. aq NH₄Cl solution. The mixture was filtered through a pad of Celite, and the salts were washed several times with Et₂O. The combined organic layers were washed with brine (2 × 20 mL) and dried over Na₂SO₄. Concentration of the Et₂O extract under reduced pressure provided 4.9 g (23.4 mmol, 94%) of a pale yellow oil, which was a 6:1 mixture of the regioisomeric diols. This mixture was dissolved in THF (60 mL) and treated with H₂O (30 mL) containing NaIO₄ (7.4 g, 34.7 mmol) with stirring to cleave the 1,2-diol. The reaction was complete in 1 h. After the layers were separated, the aq layer was extracted with Et₂O (3 × 30 mL) and the combined extracts dried over Na₂SO₄ and concentrated in vacuo. The residue was subjected to silica gel column chromatography (EtOAc-hexane, 4:6) to afford diol 17 (3.5 g, 69%) as a pale yellow liquid.

References:

Sabitha, Gowravaram;Gurumurthy;Yadav, Jhillu Singh [Synthesis,2014,vol. 46,# 1,art. no. SS-2013-Z0529-OP,p. 110 - 118]