Tributylphosphine → methyl 3-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl}phenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}benzoate

HRID 2221926ノート

反応式

HRID 2221926 の反応式
[OH:1][CH2:2][C:3]1[CH:26]=[CH:25][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=3)[C:18]([O:20][CH3:21])=[O:19])[O:12][C:13]=2[CH3:14])=[CH:5][CH:4]=1.O[C:28]1[C:32]([CH:33]=[O:34])=[CH:31][N:30]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:29]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH:33]([C:32]1[C:28]([O:1][CH2:2][C:3]2[CH:4]=[CH:5][C:6]([O:7][CH2:8][C:9]3[N:10]=[C:11]([C:15]4[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=4)[C:18]([O:20][CH3:21])=[O:19])[O:12][C:13]=3[CH3:14])=[CH:25][CH:26]=2)=[N:29][N:30]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:31]=1)=[O:34]

参加物

6

反応物 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 23076400Methyl 3-(4-{[4-(hydroxymethyl)phenoxy]methyl}-5-methyl-1,3-oxazol-2-yl)benzoateHCID 178519806HCID 178519806、化合物

生成物 1

HCID 86605863methyl 3-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl}phenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}benzoate収率 47%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of methyl 3-(4-{[4-(hydroxymethyl)phenoxy]methyl}-5-methyl-1,3-oxazol-2-yl)benzoate (1.34 g), 3-hydroxy-1-phenyl-1H-pyrazole-4-carbaldehyde (0.50 g), tributylphosphine (0.77 g) and tetrahydrofuran (100 mL) was added 1,1′-(azodicarbonyl)dipiperidine (0.96 g) was added at room temperature, and the mixture was stirred for 15 hrs. The precipitated crystals were removed by filtration and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give methyl 3-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl}phenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}benzoate as crystals (0.62 g, yield 47%) from a fraction eluted with ethyl acetate-hexane (1:2, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 161-162° C.

後処理

  1. additionwas added at room temperature
  2. customThe precipitated crystals were removed by filtration
  3. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-c7b3205fbbc641c6b0934872263c90f5
出典データセット
uspto-grants-2008_05
特許番号
US07368578B2

反応ノート

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