Methanol → 4-(2-Methoxy-5-nitrophenyl)furan-2-carbaldehyde

HRID 1593788

反応式

HRID 1593788 の反応式
I[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12].[CH:13]([C:15]1[O:16][CH:17]=[C:18](B2OC(C)(C)C(C)(C)O2)[CH:19]=1)=[O:14].CO>COCCOC.C(=O)(O)[O-].[Na+].C(OCC)(=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>[CH3:12][O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[C:18]1[CH:19]=[C:15]([CH:13]=[O:14])[O:16][CH:17]=1

参加物

9

反応物 3

HCID 887MethanolHCID 948062-Iodo-1-methoxy-4-nitrobenzeneHCID 35475414-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde

生成物 1

HCID 160991814-(2-Methoxy-5-nitrophenyl)furan-2-carbaldehyde収率 52%

試薬・触媒・溶媒 5

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a mixture of 2-iodo-4-nitroanisole (565 mg, 2.02 mmol) and 2-formylfuran-4-boronic acid pinacol ester (670 mg, 3.03 mmol) in 20 mL of ethylene glycol dimethyl ether and 12 mL of aqueous saturated sodium bicarbonate was added 80 mg of tetrakis(triphenylphosphine)palladium (0). The reaction mixture was heated at reflux overnight then allowed to cool to room temperature and added to a biphasic mixture of 10% methanol in ethyl acetate and water. The solid was collected by filtration, washed with ethyl acetate and water to provide 259 mg (52%) of 4-(2-methoxy-5-nitrophenyl)-2-furaldehyde as a light brown solid, 1H NMR (DMSO-d6) d 4.07 (s, 3H), 7.37 (d, J=9 Hz, 1H), 1H), 8.20-8.29 (m, 2H), 8.55 (d, J=3 Hz, 1H), 8.69 (s, 1H), 9.68 (s, 1H); MS 247.1 (M−H)−.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. filtrationThe solid was collected by filtration
  4. washwashed with ethyl acetate and water

出典と根拠

ORDレコード
ord-d113afc1878946c9abd432542e5f7f9e
出典データセット
uspto-grants-2007_11
特許番号
US07297795B2

関連ノート

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