Tetrahydrofuran → HCID 86719448, compound

Participants

Reaction Steps

THF (25 ml) and methanol (MeOH) (25 ml) were added to 4-{3-(triallylsilyl)propyl}benzaldehyde (4) (11.0 g, 36.9 mmol) under a nitrogen atmosphere, the mixture was cooled to around 0° C. with ice, NaBH4 (2.8 g, 73.8 mmol) was added thereto, and the mixture was stirred for 3 hours. An aqueous solution of saturated sodium hydrogen carbonate was added to the reaction mixture. The aqueous layer was extracted with diethyl ether, and the combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under a reduced pressure to give a crude product. The crude product was purified by separating by silica gel column chromatography (elution solvent: n-hexane/ethyl acetate=5/1) to give 4-{3-(triallylsilyl)propyl}benzyl alcohol (5) (yield amount: 9.2 g, yield: 84%), as shown in the following chemical reaction formula.

Provenance & Evidence