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

HRID 1039213노트

반응식

HRID 1039213 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-9ed40fa2a77f4bdeadbe738678dc7a70
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552039B2

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