Reaktion #1533563

Reaktionsgleichung

methyl 2,3-dihydrobenzofuran-2-carboxylate

methyl iodide

potassium tert-butoxide

→

title compound

2-Methyl-2,3-dihydrobenzofuran-2-carboxylic acid, methyl ester

Lösungsmittel

tetrahydrofuran

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with aqueous saturated ammonium chloride (100 mL) and water
2. 2
   Trocknendried over anhydrous sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated to dryness
5. 5
   SonstigeThe residue was purified by flash column chromatography
6. 6
   Wascheneluted with 2-5% ethyl acetate in hexane

Vorschrift

To a solution of methyl 2,3-dihydrobenzofuran-2-carboxylate (Step A, 1.0 g, 5.5 mmol) and methyl iodide (1.8 mL, 28 mmol) in 20 mL of anhydrous tetrahydrofuran at −78° C. was added potassium tert-butoxide (1 M in tetrahydrofuran, 8.4 mL, 8.4 mmol). The reaction was allowed to warm to room temperature overnight, and the resulting mixture was diluted with ethyl acetate (100 mL), washed with aqueous saturated ammonium chloride (100 mL) and water, dried over anhydrous sodium sulfate, filtered and concentrated to dryness. The residue was purified by flash column chromatography eluted with 2-5% ethyl acetate in hexane to give the title compound. 1H NMR (500 MHz, CD3OD): δ 7.16 (d, 1H), 7.12 (t, 1H), 6.86 (t, 1H), 6.76 (d, 1H), 3.75 (s, 3H), 3.58 (d, 1H), 3.17 (d, 1H), 1.66 (s, 3H).

Quelle