Ammonium Chloride → 1-(Benzyloxy)pent-4-en-2-ol

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Reaction Conditions

Reaction Steps

To a stirring 0° C. solution of 59.0 g of product from Example 1 in 375 ml of diethyl ether is added, dropwise, 432.24 ml of 1M allylmagnesiumbromide in ether. The reaction is stirred at 0° C. for 1 hour, followed by overnight stirring at room temperature. The reaction is cooledto 0° C., hydrolyzed with saturated ammonium chloride, and the layers are separated. The organic layer is washed with saturated sodium chloride, dried and concentrated in vacuo to give the product as an oil. The crude oil is purified by Kugelrohr distillation (bath temperature 100° C.) to give 61.5 g of the desired product as a colorless oil. 1H NMR(CDCl3):δ 7.34(m,5H); 5.82(m,1H); 5.08(m,2H); 4.56(s,2H); 3.88(m,1H); 3.44(ABq,2H); 2.27(t,2H); 1.7(bs, 1H).

Provenance & Evidence