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

HRID 1616609ノート

反応式

HRID 1616609 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-a12e1a36610547e89eae968001a21a2a
出典データセット
uspto-grants-2014_07
特許番号
US08765796B2

反応ノート

読み込み中…