Реакция #47683

Уравнение реакции

(S)-1-iodo-2-methyl-butane

(benzhydrylidene-amino)-acetic acid ethyl ester

potassium t-butoxide

→

(S)-2-(benzhydrylidene-amino)-4-methyl-hexanoic acid ethyl ester

Выход 74.0%

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe resulting solution stirred at 0° C. for 10 min
2. 2
   Другоеroom temperature overnight
3. 3
   КонцентрированиеThe reaction mixture was concentrated in vacuo
4. 4
   Другоеthe residue partitioned between diethyl ether and dilute aqueous hydrochloric acid
5. 5
   ДругоеThe layers were separated
6. 6
   Промывкаthe organic layer was washed with brine
7. 7
   Концентрированиеconcentrated in vacuo
8. 8
   ДругоеThe residue was purified by ISCO flash chromatography (RediSep silica 120 g, 0% to 10% ethyl acetate/hexanes) which

Методика

A solution of (benzhydrylidene-amino)-acetic acid ethyl ester (5.48 g, 20.5 mmol) in tetrahydrofuran (40 mL) was treated with potassium t-butoxide (2.83 g, 25.26 mmol) and stirred at 0° C. for 35 min. At this time a solution of (S)-1-iodo-2-methyl-butane (5.00 g, 25.25 mmol) in tetrahydrofuran (20 mL) was added via syringe and the resulting solution stirred at 0° C. for 10 min and then room temperature overnight. The reaction mixture was concentrated in vacuo and the residue partitioned between diethyl ether and dilute aqueous hydrochloric acid. The layers were separated, and the organic layer was washed with brine and concentrated in vacuo. The residue was purified by ISCO flash chromatography (RediSep silica 120 g, 0% to 10% ethyl acetate/hexanes) which afforded (S)-2-(benzhydrylidene-amino)-4-methyl-hexanoic acid ethyl ester (5.09 g, 74%) as an oil.

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