Sodium hydride → HCID 18520718, compound

Participants

Reaction Steps

3,5 g (34 mmol) of 5-hexen-1-ol, dissolved in 25 ml of THF, are added dropwise to a suspension of 0.95 g (28 mmol) of NaH in 20 ml of THF. When the addition is complete, 4.8 g (23 mmol) of hex-5-enyl 2-bromoacetate, dissolved in 15 ml of THF, are added dropwise. The mixture is then refluxed overnight. When the reaction is complete, the mixture is left to cool and quenched with 2N HCl. After the phases have separated, the aqueous phase is extracted again with Et2O and twice with EtOAc. The combined organic phases are dried over Na2SO4, filtered and evaporated on a rotary evaporator. The crude product is purified on silica gel (cyclohexane/EtOAc=40:1; Rf=0.26), giving, as product, a colorless oil in a yield of 4.8 g (67% over 2 stages).

Provenance & Evidence