1,2-Dimethoxyethane → 4-Furan-3-yl-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

HRID 29370

반응식

HRID 29370 반응식
[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14](OS(C(F)(F)F)(=O)=O)[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[O:32]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33]1.COCCOC>O>[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([C:34]3[CH:35]=[CH:36][O:32][CH:33]=3)[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 2734358Furan-3-boronic acidHCID 865990303-Methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid tert-butyl ester

생성물 1

HCID 687165134-Furan-3-yl-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester수율 68.4%

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
85 °C

실험 절차

3-Methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid tert-butyl ester (285 mg, 0.75 mmol) was mixed with K2CO3 (207 mg, 2.2 eq), furan-3-boronic acid (101 mg, 1.2 eq), Pd(Ph3)4 (43 mg, 0.05 eq), 3 mL of 1,2-dimethoxyethane and 0.5 mL of water. The mixture was heated and stirred in a 85° C. oil bath for 2 h. The reaction mixture was poured into water and was extracted with ethyl acetate. The organic extract was washed with water and dried over sodium sulfate. Removal of the solvent in vacuo gave the crude product, which was purified by column chromatography to give 153 mg of 4-furan-3-yl-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester, obtained as white solid.

후처리

  1. temperatureThe mixture was heated
  2. extractionwas extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the solvent in vacuo
  7. customgave the crude product, which
  8. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-192bf958dc894ec9b93651037a8bedf4
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420001B2

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