Hydrochloric Acid → 2-(6-((5-(4-Chlorophenyl)isoxazol-3-yl)methoxy)benzofuran-3-yl)acetic acid

HRID 1296043Notes

Reaction equation

HRID 1296043 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][CH2:15][C:16]3[CH:20]=[C:19]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=4)[O:18][N:17]=3)=[CH:13][C:8]=2[O:7][CH:6]=1.O.[OH-].[Li+].O.Cl>O1CCCC1>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]2[O:18][N:17]=[C:16]([CH2:15][O:14][C:12]3[CH:11]=[CH:10][C:9]4[C:5]([CH2:4][C:3]([OH:28])=[O:2])=[CH:6][O:7][C:8]=4[CH:13]=3)[CH:20]=2)=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 168937Lithium hydroxide, monohydrateHCID 20770854{6-[5-(4-Chloro-phenyl)-isoxazol-3-ylmethoxy]-benzofuran-3-yl}-acetic acid methyl ester

Product 1

HCID 225048572-(6-((5-(4-Chlorophenyl)isoxazol-3-yl)methoxy)benzofuran-3-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of {6-[5-(4-chloro-phenyl)-isoxazol-3-ylmethoxy]-benzofuran-3-yl}-acetic acid methyl ester (0.20 g, 0.50 mmol) in 8.0 ml of tetrahydrofuran was treated with lithium hydroxide monohydrate (0.10 g, 2.4 mmol), followed by 2.5 ml of water. The mixture was stirred at room temperature for 16 hours and added to 75 ml of water. The solution was made strongly acidic by the addition of 4.0 N hydrochloric acid. The precipitated product was extracted with ethyl acetate (4×75 ml). The combined organic layers were washed with brine (2×150 ml), then dried over anhydrous sodium sulfate and evaporated to a white solid. The crude product was recrystallized from aqueous acetonitrile. mp 193–194° C.; IR (thin film) cm−1: 1716, 1611, 1434, 1288, 1224, 1146; 400 MHz 1H NMR (DMSO-d6) 12.39 (br s, 1H), 7.87 (d, 2H, J=8.8 Hz), 7.73 (s, 1H), 7.55 (d, 2H, J=8.8 Hz), 7.44 (d, 1H, J=8.6 Hz), 7.28 (d, 1H, J=2.0 Hz), 7.19 (s, 1H), 6.93–6.96 (m, 1H), 5.24 (2, 2H), 3.59 (s, 2H); MS m/z 382 (M−1). Anal. Calc'd for C20H14ClNO5: C, 62.59; H, 3.68; N, 3.65; found: C, 62.87; H, 3.67; N, 3.61.

Workup

  1. extractionThe precipitated product was extracted with ethyl acetate (4×75 ml)
  2. washThe combined organic layers were washed with brine (2×150 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to a white solid
  5. customThe crude product was recrystallized from aqueous acetonitrile

Sources & evidence

ORD record
ord-54ff6b2643564bf1b2a0814382c9bd50
Source dataset
uspto-grants-2007_07
Patent number
US07244763B2

Reaction notes

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