Potassium Carbonate → 3-(2-Methoxyphenyl)-4,5-methylenedioxybenzaldehyde

HRID 860533

反応式

HRID 860533 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]2[O:12][CH2:11][O:10][C:9]=12)[CH:5]=[O:6].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.C(OCC)(=O)C.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>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]2[O:12][CH2:11][O:10][C:9]=12)[CH:5]=[O:6]

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 23202437-Bromo-1,3-dioxaindane-5-carbaldehydeHCID 27339582-Methoxyphenylboronic acid

生成物 1

HCID 865860323-(2-Methoxyphenyl)-4,5-methylenedioxybenzaldehyde収率 32.4%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 3-bromo-4,5-methylenedioxybenzaldehyde (2.51 g, 10.97 mmol), 2-methoxyphenylboronic acid (2.00 g, 13.16 mmol) and potassium carbonate (3.41 g, 24.68 mmol) in 1,2-dimethoxyethane (70 mL) and water (3.5 mL) was degassed with argon for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.63 g, 0.548 mmol) was added and the mixture heated at reflux under argon overnight. The solution was cooled to room temperature, diluted with ethyl acetate (100 mL) and washed successively with water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (eluent: hexane:ether, 9:1) to give 0.910 g of 3-(2-methoxyphenyl)-4,5-methylenedioxybenzaldehyde (32%) as a white solid. 1H NMR (300 MHz; CDCl3): δ 3.84 (s, 3H); 6.07 (s, 2H); 7.00–7.10 (m, 2H); 7.31 (brs, 1H); 7.30–7.45 (m, 2H); 7.53 (brs, 1H); 9.83 (s, 1H).

後処理

  1. customwas degassed with argon for 30 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux under argon overnight
  4. washwashed successively with water (50 mL) and brine (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on silica gel (eluent: hexane:ether, 9:1)

出典と根拠

ORDレコード
ord-412485adf0d14abab96b26ca4cff8025
出典データセット
uspto-grants-2006_12
特許番号
US07153875B2

関連ノート

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