Sodium Carbonate → 2-(3,5-Dimethoxy-4-methylphenyl)furan

HRID 2359192ノート

反応式

HRID 2359192 の反応式
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([CH3:15])=[C:9]([O:16][CH3:17])[CH:8]=1)(=O)=O.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1B(O)O.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[CH3:17][O:16][C:9]1[CH:8]=[C:7]([C:21]2[O:20][CH:24]=[CH:23][CH:22]=2)[CH:12]=[C:11]([O:13][CH3:14])[C:10]=1[CH3:15]

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 2734357Furan-2-boronic acidHCID 866575033,5-Dimethoxy-4-methylphenyl trifluoromethanesulfonate

生成物 1

HCID 584320242-(3,5-Dimethoxy-4-methylphenyl)furan収率 77%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

To a solution of 3,5-dimethoxy-4-methylphenyl trifluoromethanesulfonate (0.50 g, 1.67 mmol) in DME (15 mL) was added 2-furylboronic acid (0.245 g, 2.2 mmol), LiCl (0.149 g, 3.5 mmol), 2 M aqueous Na2CO3 (1.8 mL, 3.6 mmol) and tetrakis(triphenylphosphine)palladium (0.098 g, 0.085 mmol) and the mixture was degassed as described previously. The reaction was heated at 80° C. under argon for 22 hrs. After cooling to room temperature, the reaction was diluted with H2O and extracted with EtOAc. The combined organics were washed with H2O, saturated aqueous NH4Cl, H2O and brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (0-25% Et2O-hexanes) gave 2-(3,5-dimethoxy-4-methylphenyl)furan as a white solid (0.28 g, 77% yield).

後処理

  1. customthe mixture was degassed
  2. temperatureAfter cooling to room temperature
  3. additionthe reaction was diluted with H2O
  4. extractionextracted with EtOAc
  5. washThe combined organics were washed with H2O, saturated aqueous NH4Cl, H2O and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customPurification by chromatography (0-25% Et2O-hexanes)

出典と根拠

ORDレコード
ord-209f0215797e443a846dd46e05746ccb
出典データセット
uspto-grants-2014_04
特許番号
US08685975B2

反応ノート

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