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

HRID 1181027노트

반응식

HRID 1181027 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 27342152-(Di-tert-butylphosphino)biphenyl촉매HCID 1140Toluene용매

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온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f1fdd23f8ce04eb0af12911dd06f6bdf
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282501B2

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