Hydroxylamine → 7-(4-Hydroxyphenyl)-benzofuran-5-carbaldehyde oxime

HRID 1372169ノート

反応式

HRID 1372169 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[O:15][CH:14]=[CH:13][C:12]=3[CH:11]=[C:10]([CH:17]=O)[CH:9]=2)=[CH:4][CH:3]=1.[NH2:19][OH:20].CO.N1C=CC=CC=1>CCOCC>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[O:15][CH:14]=[CH:13][C:12]=3[CH:11]=[C:10]([CH:17]=[N:19][OH:20])[CH:9]=2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 787HydroxylamineHCID 887MethanolHCID 1049PyridineHCID 210717937-(4-Hydroxyphenyl)-benzofuran-5-carbaldehyde

生成物 1

HCID 854277617-(4-Hydroxyphenyl)-benzofuran-5-carbaldehyde oxime

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
68 °C

実験手順

To a 25 ml round bottom flask was added 7-(4-hydroxyphenyl)-benzofuran-5-carbaldehyde (400 mg, 1.68 mmol), hydroxylamine hydrochlorode (234 mg, 3.36 mmol), anhydrous MeOH (10.4 ml), and anhydrous pyridine (0.272 ml, 3.36 mmol). The reaction was then heated to 68° C. and the reaction was brought to reflux for 1 h. The reaction was then cooled to room temperature, dilute with ether, and the layers separated. The ether layer was washed with water, dried over anhydrous Na2SO4, passed through a silica plug, and concentrated to 410 mg (96%) product as a yellow solid. The crude material was pure by 1H NMR (−4% cis isomer was detected) and LC-MS (one peak): mp 192–194° C. 1H NMR (300 MHz, DMSO-d6): δ 6.92 (2H, d, J=8.6 Hz), 7.05 (1H, d, J=2.2 Hz), 7.69–7.72 (3H, m), 7.79 (1H, d, J=1.4 Hz), 8.09 (1H, d, J=1.1 Hz), 8.27 (1H, s), 9.74 (1H, s), 11.14 (1H, s); MS (ESI) m/z 254 ([M+H]+).

後処理

  1. temperatureto reflux for 1 h
  2. temperatureThe reaction was then cooled to room temperature
  3. customthe layers separated
  4. washThe ether layer was washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated to 410 mg (96%) product as a yellow solid

出典と根拠

ORDレコード
ord-a25e9452d262461cbe123640c7728b01
出典データセット
uspto-grants-2007_01
特許番号
US07157491B2

反応ノート

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