Tributylvinyltin → 3-Methyl-4-vinylbenzofuran-2-carboxylic acid ethyl ester

HRID 29320

反応式

HRID 29320 の反応式
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12](OS(C(F)(F)F)(=O)=O)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[CH:24]([Sn](CCCC)(CCCC)CCCC)=[CH2:25].[Cl-].[Li+]>CN(C=O)C.O.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>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:24]=[CH2:25])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

参加物

7

反応物 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 865990263-Methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid ethyl ester

生成物 1

HCID 687131603-Methyl-4-vinylbenzofuran-2-carboxylic acid ethyl ester収率 75.2%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a solution of 2.48 g (7.05 mmol) of 3-methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid ethyl ester (Example 20, Step 2) in 30 mL of DMF was added 2.16 mL (7.40 mmol) of vinyl tributyltin, 0.898 g (21.1 mmol) of lithium chloride and 0.247 g (0.352 mmol) of tetrakis(triphenylphosphine)palladium(0). The reaction was heated to 90° C. for 3 h and then cooled to room temperature. The reaction was diluted with water and extracted with ether. The combined organics were washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:25) to provide 1.22 g of 3-methyl-4-vinylbenzofuran-2-carboxylic acid ethyl ester.

後処理

  1. temperaturecooled to room temperature
  2. extractionextracted with ether
  3. washThe combined organics were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:25)

出典と根拠

ORDレコード
ord-b0c9cf25ebb547d1903fb5e5bb5ef8a5
出典データセット
uspto-grants-2008_09
特許番号
US07420001B2

関連ノート

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