Phenol → 4-(2-Benzyloxy-ethyl)-5-methyl-2-(4-phenoxy-phenyl)-oxazole

HRID 1181027ノート

反応式

HRID 1181027 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]1([OH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([O:30][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 996PhenolHCID 62657Potassium Phosphate, TribasicHCID 179843944-[2-(Benzyloxy)ethyl]-2-(4-bromophenyl)-5-methyl-1,3-oxazole

生成物 1

HCID 179843804-(2-Benzyloxy-ethyl)-5-methyl-2-(4-phenoxy-phenyl)-oxazole収率 78.9%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 27342152-(Di-tert-butylphosphino)biphenyl触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-(2-benzyloxy-ethyl)-2-(4-bromo-phenyl)-5-methyl-oxazole (0.025 mol, 9.2 g), phenol (0.03 mol, 2.8 g), K3PO4 (0.05 mol, 10.6 g), 2-(di-tert-butylphosphino)biphenyl (1.8 mmol, 0.54 g) and Pd(OAc)2 (1.2 mmol, 0.28 g) in toluene (350 mL) was degassed with nitrogen and heated at 100° C. for 18 h. Additional Pd(OAc)2 (0.5 g) and phosphine ligand (1.0 g) were added, and the mixture was heated 5 h at 100° C. The reaction was concentrated and purified directly by silica gel chromatography (4/1 hexanes/ethyl acetate) to give the title compound (7.6 g).

後処理

  1. customwas degassed with nitrogen
  2. additionAdditional Pd(OAc)2 (0.5 g) and phosphine ligand (1.0 g) were added
  3. temperaturethe mixture was heated 5 h at 100° C
  4. concentrationThe reaction was concentrated
  5. custompurified directly by silica gel chromatography (4/1 hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-f1fdd23f8ce04eb0af12911dd06f6bdf
出典データセット
uspto-grants-2007_10
特許番号
US07282501B2

反応ノート

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