Dichloromethane → Ethyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-methoxy-benzoate

HRID 2177710ノート

反応式

HRID 2177710 の反応式
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH3:23])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:25]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26]1.C(Cl)Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH3:23])[C:14]([C:27]3[CH:28]=[CH:29][O:25][CH:26]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 2734358Furan-3-boronic acidHCID 67107394Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate2 回

生成物 1

HCID 67107652Ethyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-methoxy-benzoate収率 63.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
140 °C

実験手順

A mixture of ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate (Intermediate 61, 0.13 g), furan-3-yl boronic acid (0.036 g), palladium chloride dppf adduct with DCM (0.026 g) and cesium carbonate (0.3 g) in THF (3.5 ml) and water (0.5 ml) was sealed in a microwave vial and degassed. The mixture was then heated in the microwave at 140° C. for 10 minutes. After cooling, the mixture was poured into water and extracted with ethyl acetate. The organic phase was dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60% to give ethyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-methoxy-benzoate (0.08 g) as a colourless gum.

後処理

  1. customwas sealed in a microwave vial and
  2. customdegassed
  3. temperatureAfter cooling
  4. additionthe mixture was poured into water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was purified by chromatography on silica
  10. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60%

出典と根拠

ORDレコード
ord-407be453a39246a0b9d20a1d917a05d1
出典データセット
uspto-grants-2015_06
特許番号
US09067905B2

反応ノート

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