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

HRID 1593788

반응식

HRID 1593788 반응식
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

참가 물질

9

반응물 3

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

생성물 1

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

시약·촉매·용매 5

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

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)−.

후처리

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

출처 및 근거

ORD 기록
ord-d113afc1878946c9abd432542e5f7f9e
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297795B2

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