Triethylamine → 4-[5-(2-Methoxy-phenyl)-isoxazol-3-yl]-butyric acid methyl ester

HRID 1616609Notes

Reaction equation

HRID 1616609 reaction equation
C1(N=C=O)C=CC(N=C=O)=CC=1.[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22])#[CH:14].[CH3:23][O:24][C:25](=[O:33])[CH2:26][CH2:27][CH2:28][CH2:29][N+:30]([O-])=[O:31].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:23][O:24][C:25](=[O:33])[CH2:26][CH2:27][CH2:28][C:29]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])[O:31][N:30]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 610091,4-DiisocyanatobenzeneHCID 543911Methyl 5-nitropentanoateHCID 5829121-Ethynyl-2-methoxybenzene

Product 1

HCID 591677844-[5-(2-Methoxy-phenyl)-isoxazol-3-yl]-butyric acid methyl esterYield 112.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add 1,4-phenylenediisocyanate (19.22 g, 120.0 mmol) to a stirred solution of 1-ethynyl-2-methoxy-benzene (2204901, 5.29 g, 40.0 mmol) and 5-nitro-pentanoic acid methyl ester (7.91 g, 49.1 mmol) in toluene (300 mL, anhydrous) and stir under N2. Add triethylamine (16.7 mL, 120.0 mmol) and heat to reflux under N2 overnight. Filter mixture through a pad of Celite® and rinse with toluene. Concentrate to get 12.4 g yellow oil. Adsorb on SiO2 and purify the residue by flash chromatography on silica gel eluting with 0-30% EtOAc/hexanes to afford the title compound (14.0 g, 74%). MS (IS) 276 (M+1)+.

Workup

  1. temperatureto reflux under N2 overnight
  2. filtrationFilter mixture through a pad of Celite®
  3. washrinse with toluene
  4. concentrationConcentrate

Sources & evidence

ORD record
ord-a12e1a36610547e89eae968001a21a2a
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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