Acetyl chloride → HCID 69508183, compound

HRID 1375686Notes

Reaction equation

HRID 1375686 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:5][O:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([I:14])[CH:9]=1.[C:20](Cl)(=[O:22])[CH3:21]>N1C=CC=CC=1>[C:20]([O:1][CH2:2][C:3]1[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:5][O:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([I:14])[CH:9]=1)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 45117062HCID 45117062, compound

Product 1

HCID 69508183HCID 69508183, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 4-(hydroxymethyl)-5-(3-iodophenyl)isoxazole-3-carboxylate (1.50 g, 4.03 mmol) in pyridine (5 mL) was stirred for 10 min. followed by cooling to 0° C. and slowly adding acetyl chloride (379 mg, 4.83 mmol). The mixture was allowed to come to ambient temperature and stirred for 2 hours. The solvent was removed under vacuo and the mixture purified by column chromatography (0–30% ethyl acetate in hexanes) to provide the titled compound (1.65 g, 99%).

Workup

  1. customto come to ambient temperature
  2. customThe solvent was removed under vacuo
  3. customthe mixture purified by column chromatography (0–30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1817b78d70a04fafb1c57258d77545f8
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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