反応式
[H-].[Na+].[CH2:3](Br)[CH:4]=[CH2:5].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:17][CH2:18][CH:19]2[CH2:23][C:22]3[CH:24]=[C:25]([Cl:32])[CH:26]=[C:27]([O:28]CC=C)[C:21]=3[O:20]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1.C(OCC=C)C=C>C1(C)C=C(C)C=C(C)C=1>[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([S:14]([O:17][CH2:18][CH:19]2[CH2:23][C:22]3[CH:24]=[C:25]([Cl:32])[C:26]([CH2:5][CH:4]=[CH2:3])=[C:27]([OH:28])[C:21]=3[O:20]2)(=[O:15])=[O:16])=[CH:12][CH:13]=1参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
実験手順
Treatment of (±)-(5-chloro-7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (22.1 g, 0.06 mol) with hydrogen bromide (30 wt. % in acetic acid, 400 mL) followed by potassium carbonate (4.15 g, 0.03 mol) provided (±)-(5-chloro-7-hydroxy-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as a brown oil. Treatment of the phenyl with sodium hydride (3.2 g, 0.053 mol) and allyl bromide (6.4 g, 0.053 mol) generally according to the procedure described for Intermediate 37 afforded (±)-[7-(allyloxy)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate. Treatment of the allyl ether in refluxing mesitylene (250 mL) generally according to the procedure described for Intermediate 1 afforded 4.5 g (19%) of (±)-(6-allyl-5-chloro-7-hydroxy-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as a pale yellow solid. mp 128-131° C.; Anal. calcd. for C19H19ClO5S: C, 57.79; H, 4.85. Found: C, 58.28; H, 4.68.
出典と根拠
- ORDレコード
- ord-915bad71be814b72805d8eafffe38984
- 出典データセット
- uspto-grants-2010_06
- 特許番号
- US07728155B2
関連ノート
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