In the presence of metallic strontium, the Barbier-type alkylation of aldehydes with alkyl iodides proceeded smoothly at −15 °C under an argon atmosphere to afford the corresponding alkylated alcohols in moderate to good yields. The unusual addition reaction of ethyl benzoate with tert-butyl iodide took place to give the p-tert-butylated alkylated product (the 1,6-adduct of the benzoate) in 55% yield. Using strontium isopropoxide, the Meerwein–Ponndorf–Verley-type reduction of the aldehyde proceeded smoothly under reflux conditions in 2-propanol.
Addition reactions
Addition reactions O 0060The Barbier-Type Alkylation of Aldehydes with Alkyl Halides in the Presence of Metallic Strontium. -In the presence of metallic Sr the Barbier-type alkylation of aldehydes (I) with iodides (II) proceeds smoothly to afford the corresponding alkylated alcohols (III) in moderate to good yields. Using strontium isopropoxide, the Meerwein-Ponndorf-Verley-type reduction of aldehyde (Ia) gives the primary alcohol (IV). -(MIYOSHI*, N.; KAMIURA, K.; OKA, H.; KITA, A.; KUWATA, R.; IKEHARA, D.; WADA, M.; Bull. Chem. Soc. Jpn. 77 (2004) 2, 341-345; Dep. Chem., Fac. Integr. Arts Sci., Univ. Tokushima, Minamijosanjima, Tokushima 770, Japan; Eng.) -M. Paetzel 22-042
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