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

HRID 2113886노트

반응식

HRID 2113886 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매2회

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온도
40 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d3699187efa9492f8d7af6088717a3ee
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432291B2

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