Réaction #47683

Équation de réaction

(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

Rendement 74.0%

Solvants

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source