Réaction #984

Équation de réaction

aldehyde

4-Formylbenzoic acid methyl ester

[1-(1,3-dioxan-2-yl)ethyl]triphenylphosphoniumbromide

n-BuLi

→

olefin

Rendement 50.3%

4-[3-[1,3]-Dioxolan-2-yl -propenyl)benzoic acid methyl ester

Rendement 50.3%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   LavageFlash chromatography (elution with 10% ethyl acetate in hexane)

Mode opératoire

The olefin was prepared from 4.3 g (26.2 mmol) of the aldehyde 167, 13.94 g of [1-(1,3-dioxan-2-yl)ethyl]triphenylphosphoniumbromide and 12.6 mL (32.0 mmol) of n-BuLi in 75 mL of THF as described for the synthesis of 156 in Example 8. Flash chromatography (elution with 10% ethyl acetate in hexane) gave 3.27 g of the olefin 168. 1H NMR consistent with the product.

Source