Diethyl Ether → Benzofuran-5-yl(phenyl)methanol

HRID 2075191

反応式

HRID 2075191 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[C:12]1([Mg]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OCC)C>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[OH:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 27738751-Benzofuran-5-carbaldehydeHCID 178418255HCID 178418255、化合物

生成物 1

HCID 58415371Benzofuran-5-yl(phenyl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-benzofuran-5-carbaldehyde (2.70 g, 18.5 mmol) in 50 mL THF under N2 was added phenylmagnesium bromide 3.0M solution in diethyl ether (7.39 mL, 22.2 mmol). The reaction was allowed to stir for 1 h, then was quenched with NH4Cl sat'd aq., extracted with diethyl ether, washed with brine, dried over anhyd. sodium sulfate, filtered, and concentrated in vacuo to a solid to give benzofuran-5-yl(phenyl)methanol which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.94 (d, J=2.0 Hz, 1H), δ 7.64 (s, 1H), 7.49 (d, J=8.5 Hz, 1H), 7.36-7.42 (m, 2H), 7.26-7.33 (m, 3H), 7.19 (t, J=7.3 Hz, 1H), 6.92 (d, J=1.5 Hz, 1H), 5.88 (d, J=4.0 Hz, 1H), 5.77-5.83 (m, 1H).

後処理

  1. customwas quenched with NH4Cl sat'd aq.
  2. extractionextracted with diethyl ether
  3. washwashed with brine
  4. customdried over anhyd
  5. filtrationsodium sulfate, filtered
  6. concentrationconcentrated in vacuo to a solid

出典と根拠

ORDレコード
ord-2bb8768110694cde84453063495b7b0f
出典データセット
uspto-grants-2011_04
特許番号
US07919519B2

関連ノート

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