1-Phenyl-1-hexyne → Methyl 4-butyl-5-phenylisoxazole-3-carboxylate

HRID 1804453

反応式

HRID 1804453 の反応式
[C:1]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].[N+:13]([CH:16](C(OC)=O)[C:17]([O:19][CH3:20])=[O:18])([O-])=[O:14].F[P-](F)(F)(F)(F)F.C([N+]1C=CN(C)C=1)CCC>C1(C)C=CC=CC=1>[CH2:3]([C:2]1[C:16]([C:17]([O:19][CH3:20])=[O:18])=[N:13][O:14][C:1]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH2:4][CH2:5][CH3:6]

参加物

5

反応物 3

HCID 1369081-Phenyl-1-hexyneHCID 226085Dimethyl nitromalonateHCID 27341741-Butyl-3-methylimidazolium hexafluorophosphate

生成物 1

HCID 58537207Methyl 4-butyl-5-phenylisoxazole-3-carboxylate収率 34.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of hex-1-ynylbenzene (0.274 mL, 1.56 mmol), dimethyl 2-nitromalonate (0.421 mL, 3.12 mmol), 1-butyl-3-methylimidazoliumhexafluorophosphate (0.032 mL, 0.156 mmol) in toluene (6 mL) was subjected to the microwave at 170° C. for 150 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash silica gel chromatography using 5% ethyl acetate in hexane to give methyl 4-butyl-5-phenylisoxazole-3-carboxylate (0.142 g, 0.531 mmol, 34.1% yield) as a clear, colorless oil. The product was 97% pure by HPLC with a ret. time=3.11 min.−Column. CHROMOLITH® SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1=260.2.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash silica gel chromatography

出典と根拠

ORDレコード
ord-4f0dc6e6b8c54f4faab1548759712f2b
出典データセット
uspto-grants-2013_01
特許番号
US08354398B2

関連ノート

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