Water → HCID 59340933, Verbindung

Temperatur

90 °C

The mixture of ethyl 3-(4-hydroxyphenyl)-5-methylisoxazole-4-carboxylate (Preparation C) (0.474 g, 1.92 mmol), Cs2CO3 (0.937 g, 2.88 mmol) and allyl bromide (0.27 mL, 3.12 mmol) in 10 mL of THF was sealed in a 150-mL pressure vessel and stirred at 90° C. overnight. The reaction mixture was cooled to room temperature. Water (150 mL) and ethyl acetate (150 mL) were added to the reaction mixture. Layers were separated and the aqueous layer was extracted with ethyl acetate (150 mL). The combined organic extract was dried over anhydrous sodium sulfate. Solvent was evaporated in vacuo to give 0.66 g of crude product, which was used in the next step without purification. LCMS (method B) RT 3.34 min., MH+288. 1H NMR (500 MHz, CDCl3) δ 7.58 (d, J=8.5Hz, 2H), 6.96 (d, J=8.5Hz, 2H), 6.12-6.00 (m, 1H), 5.46-5.26 (m, 2H), 4.58 (d, J=5.2Hz, 2H), 4.25 (q, J=7.2Hz, 2H), 2.71 (s, 3H), 1.25 (t, J=7.2 Hz, 3H).

1. customwas sealed in a 150-mL pressure vessel
2. temperatureThe reaction mixture was cooled to room temperature
3. customLayers were separated
4. extractionthe aqueous layer was extracted with ethyl acetate (150 mL)
5. extractionThe combined organic extract
6. dry with materialwas dried over anhydrous sodium sulfate
7. customSolvent was evaporated in vacuo

ORD-Eintrag

ord-8487838b06404903b95d810bad2f1c8f

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07732434B2