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

HRID 29320

반응식

HRID 29320 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b0c9cf25ebb547d1903fb5e5bb5ef8a5
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420001B2

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