Water → HCID 59340933, compound

HRID 14402Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([CH3:18])[O:10][N:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:25](Br)[CH:26]=[CH2:27].O>C1COCC1.C(OCC)(=O)C>[CH2:27]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([CH3:18])[O:10][N:9]=2)=[CH:6][CH:7]=1)[CH:26]=[CH2:25]

Participants

Conditions

Temperature: 90 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-8487838b06404903b95d810bad2f1c8f
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732434B2

Reaction notes

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