Tin tetrachloride → 1-[2-(6-Methoxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone

HRID 1359207ノート

反応式

HRID 1359207 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[CH:17]=1)[CH:7]=[CH:6]2.[C:22](Cl)(=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25].[Sn](Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[C:17]=1[C:22](=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25])[CH:7]=[CH:6]2

参加物

5

反応物 3

HCID 24287Tin tetrachlorideHCID 66054Isovaleryl chlorideHCID 110766242-(6-Methoxy-2-naphthyl)-1-benzofuran

生成物 1

HCID 181827841-[2-(6-Methoxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

Following the procedure described in Step 2 of Example 1, 2-(6-methoxy-2-naphthyl)-1-benzofuran (3.00 g, 10.9 mmol), was acylated with isovaleryl chloride (1.9 mL, 16 mmol), in presence of tin (IV) chloride (1.7 mL, 14 mmol) in chloroform (60 mL). Purification by flash chromatography using 15-100% chloroform in hexane as an eluant then by using the Biotage apparatus using 1.5% ethyl acetate in hexane as an eluant yielded the title compound as a yellow wax (1.34 g); 1HNMR (200 MHz, DMSO-d6): δ8.35 (s, 1H), 8.0 (d, 3H, J=8.2 Hz), 7.8 (d, 1H, J=10.2 Hz), 7.7 (d, 1H, J=7.7 Hz), 7.35-7.55 (m, 3H), 7.3 (d, 1H, J=8.7 Hz), 3.95 (s, 3H), 2.6 (d, 2H, J=7.7 Hz), 2.0-2.1 (m, 1H), and 0.75 ppm (d, 6H, J=7.7 Hz).

後処理

  1. customPurification by flash chromatography

出典と根拠

ORDレコード
ord-142eea6ab14b40a787bbe2db0bd48c25
出典データセット
uspto-grants-2003_07
特許番号
US06599925B2

反応ノート

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