Dichloromethane → Ethyl 6-(benzenesulphonylmethyl)-2-methoxy-3-methylbenzoate

HRID 2177709ノート

反応式

HRID 2177709 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.[CH2:25](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]([CH3:25])=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 3

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

生成物 1

HCID 67107517Ethyl 6-(benzenesulphonylmethyl)-2-methoxy-3-methylbenzoate収率 18.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
160 °C

実験手順

A mixture of ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate (Intermediate 61, 0.332 g), potassium methyltrifluoro borate (0.0675 g), palladium chloride dppf adduct with DCM (0.066 g) and cesium carbonate (0.786 g) in THF (9 ml) and water (1 ml) was sealed in a microwave vial and degassed. The mixture was then heated in the microwave at 160° C. for 30 minutes. After cooling, the mixture was dried (MgSO4) and filtered through Celite, and the pad was washed with ethyl acetate. 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 0-50% to give ethyl 6-(benzenesulphonylmethyl)-2-methoxy-3-methylbenzoate (0.05 g) as a colourless gum.

後処理

  1. customwas sealed in a microwave vial and
  2. customdegassed
  3. temperatureAfter cooling
  4. dry with materialthe mixture was dried (MgSO4)
  5. filtrationfiltered through Celite
  6. washthe pad was washed with ethyl acetate
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by chromatography on silica
  9. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-50%

出典と根拠

ORDレコード
ord-81ccf3ebe8c9443e81683b601bfa33d9
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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