Water → ethyl (2E)-3-(2-methyl-2H-indazol-4-yl)acrylate

HRID 1639745노트

반응식

HRID 1639745 반응식
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH3:17][N:18]1[CH:26]=[C:25]2[C:20]([CH:21]=[CH:22][CH:23]=[C:24]2[CH:27]=O)=[N:19]1.O>O1CCCC1>[CH3:17][N:18]1[CH:26]=[C:25]2[C:20]([CH:21]=[CH:22][CH:23]=[C:24]2/[CH:27]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:19]1

참가 물질

6

반응물 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 593346182-Methyl-2H-indazole-4-carbaldehyde

생성물 1

HCID 66720667ethyl (2E)-3-(2-methyl-2H-indazol-4-yl)acrylate수율 98.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

Under nitrogen atmosphere, to a suspension of sodium hydride (1.26 g, 31.5 mmol) in tetrahydrofuran (50 mL) was added a solution of ethyl diethylphosphonoacetate (7.06 g, 31.5 mmol) in tetrahydrofuran (50 mL) at 0° C., and the mixture is was stirred for 20 min. To the reaction mixture was added a solution of 2-methyl-2H-indazole-4-carbaldehyde (4.60 g, 28.7 mmol) in tetrahydrofuran (100 mL), and the mixture was warmed to room temperature over 2 hr. Water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) to give the title compound (6.50 g, yield 98%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1)

출처 및 근거

ORD 기록
ord-e4cce467a1f74183bef4ce8b8bafa0a8
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110585B2

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