Triethylamine → HCID 57780766, compound

HRID 1668436Notes

Reaction equation

HRID 1668436 reaction equation
[Cl:1][C:2]1[O:6][C:5]([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([CH2:18][OH:19])[O:9][N:8]=2)=[CH:4][CH:3]=1.CCN([CH2:25][CH3:26])CC.C([O-])(O)=[O:28].[Na+]>CC(OC(C)=O)=O>[C:25]([O:19][CH2:18][C:10]1[O:9][N:8]=[C:7]([C:5]2[O:6][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:28])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 57780767HCID 57780767, compound

Product 1

HCID 57780766HCID 57780766, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 3-(5-chlorofuran-2-yl)-4-phenyl-5-hydroxymethylisoxazole (350 mg, 1.273 mmoli) in Ac2O (5.2 ml), kept stirring at 0° C., is added Et3N (0.213 ml, 1.531 mmole). The mixture is brought to ambient temperature and kept stirring for 1.5 h. The reaction is blocked by adding ice and 10 ml of saturated solution of NaHCO3. The two phases are separated and the aqueous phase is extracted three times with methylene chloride. The combined organic extracts are dried over Na2SO4 and the solvent distilled in a vacuum. The residue subjected to column chromatography (silica gel, petroleum ether/ethyl acetate=9:1, and 8:2 after the elution of the first substance) gives 237 mg of oily product with a yield of 60%. FT-IR (neat): 3132, 3053, 2921, 1751, 1636, 1517, 1432, 1412, 1372, 1359, 1226, 1127, 1048, 1018, 985, 939, 903, 790, 777, 704 cm−1. 1H NMR (400 MHz, CDCl3, δ): 7.44-7.42 (m, 3H, aromatic protons); 7.30-7.28 (m, 2H, aromatic protons); 6.24 (d, J=3.6 Hz, 1H, furyl proton); 6.11 (d, J=3.6 Hz, 1H, furyl proton); 5.07 (s, 2H, CH2); 2.02 (s, 3H, CH3).13C NMR (75 MHz, CDCl3, δ): 170.3, 163.5, 152.7, 143.1, 139.0, 130.2, 129.2, 129.2, 128.2, 118.2, 114.4, 108.2, 55.4, 20.7. GC-MS (70 eV) m/z (rel.int.): 319 [M(37Cl)+, 33], 317 [M(35Cl)+, 90], 277 (18), 276 (10), 275 (49), 240 (18), 238 (10), 217 (23), 216 (11), 213 (17), 212 (100), 211 (32), 190 (11), 188 (27), 182 (11), 154 (20), 153 (26), 152 (21), 129 (15), 127 (19), 91 (12), 89 (26), 73 (11), 43 (30). Anal. Calc. for C16H12ClNO3: C, 64.48; H, 3.81; N, 4.41. Found: C, 64.46; H, 3.82; N, 4.46.

Workup

  1. customis brought to ambient temperature
  2. customThe two phases are separated
  3. extractionthe aqueous phase is extracted three times with methylene chloride
  4. dry with materialThe combined organic extracts are dried over Na2SO4
  5. distillationthe solvent distilled in a vacuum
  6. washafter the elution of the first substance)

Sources & evidence

ORD record
ord-5c13ea03ddb1494b8b59eac55ed8480a
Source dataset
uspto-grants-2011_08
Patent number
US07989450B2

Reaction notes

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