Methyl 6-chloro-6-oxohexanoate → HCID 59167745, compound

HRID 1616558Notes

Reaction equation

HRID 1616558 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](Cl)=[O:9].O[NH:13][C:14](=[NH:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22]>N1C=CC=CC=1.O>[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][N:23]=[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])[N:13]=1

Participants

5

Reactant 2

HCID 520737Methyl 6-chloro-6-oxohexanoateHCID 178489516HCID 178489516, compound

Product 1

HCID 59167745HCID 59167745, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Add 5-chlorocarbonylpentanoic acid methyl ester (15.30 g, 86 mmol) to a solution of N-hydroxy-2-methoxybenzamidine (12.0 g, 71 mmol) in pyridine (40 mL) and under nitrogen at a rate to keep the mixture at a gentle reflux. Then, heat the mixture at reflux for 4 hours. Dilute the mixture with water (300 mL) and extract with methylene chloride (3×200 mL). Wash the combined organic extracts with brine (100 mL), dry over sodium sulfate and remove the solvent under reduced pressure. Purify the residue by flash column chromatography on silica gel, eluting with ethyl acetate/hexanes (1:19), to afford 5-[3-(2-methoxyphenyl)-[1,2,4]oxadiazol-5-yl]pentanoic acid methyl ester (12.8 g, 55%).

Workup

  1. temperatureThen, heat the mixture
  2. temperatureat reflux for 4 hours
  3. extractionextract with methylene chloride (3×200 mL)
  4. washWash the combined organic extracts with brine (100 mL)
  5. dry with materialdry over sodium sulfate
  6. customremove the solvent under reduced pressure
  7. customPurify the residue by flash column chromatography on silica gel
  8. washeluting with ethyl acetate/hexanes (1:19)

Sources & evidence

ORD record
ord-20f3b67a71ed41e68180e9264964729c
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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