Réaction #499888

Équation de réaction

ethyl salicylate

cesium carbonate

dimethylformamide

tert-butyl 4-chlorobutyrate

→

ethyl 2-(3-tert-butoxycarbonylpropoxy)benzoate

Rendement 62.0%

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   AutreThe mixture was partitioned between ethyl ether (100 mL) and water
2. 2
   Autrethe organic layer was separated
3. 3
   Lavagewashed with additional water (3×) and saturated aqueous sodium chloride
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo
7. 7
   Autreto afford a colorless oil
8. 8
   AutreThe residue was purified by silica gel flash chromatography

Mode opératoire

A mixture comprising ethyl salicylate (3.14 g, 18.9 mmol) and cesium carbonate (6.2 g, 18.9 mmol), dimethylformamide (25 mL) and tert-butyl 4-chlorobutyrate (4.08 g, 22.8 mmol) was heated at 70° C. and stirred for 12 hours. The mixture was partitioned between ethyl ether (100 mL) and water and the organic layer was separated and washed with additional water (3×) and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford a colorless oil. The residue was purified by silica gel flash chromatography using pure hexane to (10:1) hexane:ethyl acetate to provide ethyl 2-(3-tert-butoxycarbonylpropoxy)benzoate (3.6 g, 62% yield) as a colorless oil; 1H NMR (300 MHz, CDCl3): 7.80 (d, 1H), 7.49 (tr, 1H), 7.00 (m, 2H), 4.40 (q, 2H), 4.10 (tr, 2H), 2.50 (tr, 2H), 2.10 (m, 2H), 1.45 (s, 9H), 1.40 (tr, 3H).

Source