Thionyl Chloride → 6-(Chloromethyl)-2,3-dihydrobenzofuran
反応式
[O:1]1[C:5]2[CH:6]=[C:7]([CH2:10]O)[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.O=S(Cl)[Cl:14]>C(Cl)(Cl)Cl>[Cl:14][CH2:10][C:7]1[CH:8]=[CH:9][C:4]2[CH2:3][CH2:2][O:1][C:5]=2[CH:6]=1参加物
4
実験手順
To a solution of (2,3-dihydrobenzofuran-6-yl)methanol (13.8 g, 92 mmol) in CHCl3 (200 mL) was slowly added SOCl2 at 0□. The reaction mixture was stirred at reflux for 4 h. After the solvent was removed, saturated NaHCO3 and ethyl acetate were added to the mixture. The organic layer was extracted with ethyl acetate. The combined organic layer was then washed with brine and dried over Na2SO4, filtered and concentrated to afford 6-(chloromethyl)-2,3-dihydrobenzofuran (12.3 g, 80.0% yield). 1H NMR (400 MHz, CDCl3) δ: 7.16 (d, J=7.5, 1H), 6.87 (d, J=7.5, 1H), 6.83 (s, 1H), 4.58 (t, J=8.7, 2H), 4.49 (s, 2H), 3.20 (t, J=8.7, 2H).
後処理
- temperatureat reflux for 4 h
- customAfter the solvent was removed
- additionsaturated NaHCO3 and ethyl acetate were added to the mixture
- extractionThe organic layer was extracted with ethyl acetate
- washThe combined organic layer was then washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
出典と根拠
- ORDレコード
- ord-6871aa3dce0d4047ace83bf9b4ca038f
- 出典データセット
- uspto-grants-2015_03
- 特許番号
- US08969386B2
反応ノート
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