Triethylamine → 5-[5-(5-Chloro-2-methoxy-phenyl)-isoxazol-3-yl]-pentanoic acid ethyl ester

HRID 1443711ノート

反応式

HRID 1443711 の反応式
C1(N=C=O)C=CC(N=C=O)=CC=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([C:22]#[CH:23])[CH:15]=1.[CH2:24]([O:26][C:27](=[O:36])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][N+:33]([O-])=[O:34])[CH3:25].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:24]([O:26][C:27](=[O:36])[CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:23]=[C:22]([C:16]2[CH:15]=[C:14]([Cl:13])[CH:19]=[CH:18][C:17]=2[O:20][CH3:21])[O:34][N:33]=1)[CH3:25]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 610091,4-DiisocyanatobenzeneHCID 13717120Ethyl 6-nitrohexanoateHCID 232607034-Chloro-2-ethynyl-1-methoxybenzene

生成物 1

HCID 591677645-[5-(5-Chloro-2-methoxy-phenyl)-isoxazol-3-yl]-pentanoic acid ethyl ester収率 64.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Add 1,4-phenylenediisocyanate (8.41 g, 52.5 mmol) to a stirred solution of 4-chloro-2-ethynyl-1-methoxy-benzene (4.0 g, 30.3 mmol) and 6-nitro-hexanoic acid ethyl ester (8.6 g, 45.4 mmol) in toluene (300 mL, anhydrous) and stir at room temperature under N2. Add triethylamine (7.3 mL, 52.5 mmol) and heat to reflux under N2 overnight. Filter mixture through a pad of Celite® and rinse with toluene. Concentrate to get 6.6 g of a orange oil. Adsorb on SiO2 and purify the residue by flash chromatography on silica gel eluting with 0-40% EtOAc/hexanes to afford the title compound (4.51 g, 76%). MS (IS) 338 (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-317ea096f36a41729f7ebe3d44984a57
出典データセット
uspto-grants-2010_02
特許番号
US07662771B2

反応ノート

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