Dimethylbarbituric acid → 3-Methyl-4-(2-[1,2,3]triazol-1-yl-ethoxymethyl)-phenol

HRID 2113886ノート

反応式

HRID 2113886 の反応式
C([O:4][C:5]1[CH:19]=[CH:18][C:8]([CH2:9][O:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[N:14]2)=[C:7]([CH3:20])[CH:6]=1)C=C.CN1C(=O)CC(=O)N(C)C1=O>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:20][C:7]1[CH:6]=[C:5]([OH:4])[CH:19]=[CH:18][C:8]=1[CH2:9][O:10][CH2:11][CH2:12][N:13]1[CH:17]=[CH:16][N:15]=[N:14]1

参加物

5

反応物 2

HCID 69860Dimethylbarbituric acidHCID 692933751-[2-(4-Allyloxy-2-methyl-benzyloxy)-ethyl]-1H-[1,2,3]triazole

生成物 1

HCID 692910153-Methyl-4-(2-[1,2,3]triazol-1-yl-ethoxymethyl)-phenol収率 53%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
40 °C

実験手順

A solution of 7.30 g (26.7. mmol) 1-[2-(4-Allyloxy-2-methyl-benzyloxy)-ethyl]-1H-[1,2,3]-triazole in 100 ml dichloromethane was added to a solution of 13.02 g (83.4 mmol) 1,3-dimethylbarbituric acid an 959 mg (0.8 mmol) Pd(PPh3)4 in 30 ml dichloromethane and stirred overnight at 40° C. The mixture was extracted with 3× sat. NaHCO3-solution. The combined aqueous phases were extracted with dichloromethane. The combined organic extracts were dried over Na2SO4. Solvents were distilled off and the residue was purified by chromatography on silica gel (heptane/ethyl acetate 1/1 to 0/1) to yield 3.30 g (53%) 3-Methyl-4-(2-[1,2,3]triazol-1-yl-ethoxymethyl)-phenol as a yellow solid melting at 92-93° C.

後処理

  1. extractionThe mixture was extracted with 3× sat. NaHCO3-solution
  2. extractionThe combined aqueous phases were extracted with dichloromethane
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. distillationSolvents were distilled off
  5. customthe residue was purified by chromatography on silica gel (heptane/ethyl acetate 1/1 to 0/1)

出典と根拠

ORDレコード
ord-d3699187efa9492f8d7af6088717a3ee
出典データセット
uspto-grants-2008_10
特許番号
US07432291B2

反応ノート

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