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

HRID 29370

反応式

HRID 29370 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
85 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-192bf958dc894ec9b93651037a8bedf4
出典データセット
uspto-grants-2008_09
特許番号
US07420001B2

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