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Tin tetrachloride → Ethyl 2-{[1-methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate

HRID 1359228
ノート
印刷プレビュー

反応式

HRID 1359228 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([CH3:20])=[C:15]([O:21][CH:22]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:14]=[CH:13]2.[C:35](Cl)(=[O:40])[CH2:36][CH2:37][CH2:38][CH3:39].[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:20][C:16]1[C:17]2[C:12](=[CH:11][C:10]([C:2]3[O:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[C:3]=3[C:35](=[O:40])[CH2:36][CH2:37][CH2:38][CH3:39])=[CH:19][CH:18]=2)[CH:13]=[CH:14][C:15]=1[O:21][CH:22]([CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 24287Tin tetrachlorideHCID 61186Valeryl chlorideHCID 516892Sodium BicarbonateHCID 18182810Ethyl 2-{[6-(1-benzofuran-2-yl)-1-methyl-2-naphthyl]oxy}-3-phenylpropanoate

生成物 1

HCID 12082839Ethyl 2-{[1-methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate収率 49.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a mixture of ethyl 2-{[6-(1-benzofuran-2-yl)-1-methyl-2-naphthyl]oxy}-3-phenylpropanoate (0.944 g, 2.10 mmol) in methylene chloride (4.2 mL) at −78° C. was added valeryl chloride (0.25 mL, 2.1 mmol), and tin (IV) chloride (0.25 mL, 2.1 mmol). The reaction mixture was stirred for 2 hours and 20 minutes. It was diluted with extra methylene chloride and poured into excess sodium bicarbonate solution. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The compound was purified by flash chromatography using 100% hexane and 0.5-3% ethyl acetate in hexane. It was dried at 60° C. for 30 minutes to afford ethyl 2-{[1-methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate as a yellow gum (0.553 g). Mass spectrum (+ESI, [M+H]+) m/z 5351HNMR (500 MHz, DMSO-d6): δ8.35 (d, 1H, J=1.7 Hz), 8.1 (d, 1H, J=9.0 Hz), 8.05 (dd, 1H, J=7.6 Hz and 1.0 Hz), 7.9 (d, 1H, J=9.2 Hz), 7.85 (dd, 1H, J=8.9 Hz and 1.8 Hz), 7.75 (d, 1H, J=8.1 Hz), 7.25-7.45 (m, 8H), 5.3-5.35 (m, 1H), 4.1 (q, 2H, J=6.9 Hz), 3.25-3.35 (m, 2H), 2.75 (t, 2H, J=7.3 Hz), 2.5 (s, 3H), 1.5-1.6 (m, 2H), 1.05-1.2 (m, 5H), and 0.7 ppm (t, 3H, J=7.4 Hz). Elemental Analysis for C35H34O5: Calculated: C, 78.63; H, 6.41; N, 0.00. Found: C, 78.70; H, 6.30; N, 0.00.

後処理

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe compound was purified by flash chromatography
  6. customIt was dried at 60° C. for 30 minutes

出典と根拠

ORDレコード
ord-4e477961c660405787ce6ae906518ace
出典データセット
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06599925B2

反応ノート

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