Diisobutylaluminum hydride → 6-Bromo-1,3-dihydroisobenzofuran-1-ol
反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][O:7][C:8]2=[O:9])=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>ClCCl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][O:7][CH:8]2[OH:9])=[CH:4][CH:3]=1参加物
4
反応条件
- 温度
- -78 °C
実験手順
Step 1) To a solution of 6-bromophthalide (144, 550 mg, 2.58 mmol) in dichloromethane (20.0 mL) was slowly added DIBAL-H (2.7 mL, 1.0M solution in hexane) at −78° C., and the reaction mixture was stirred for 1.5 h at −78° C. The resulting mixture was quenched with sat. Na2SO4 and allowed to warm to room temperature. To the mixture was added anhydrous Na2SO4, and the mixture was stirred for 12 h, then filtered and concentrated in vacuo. The crude was purified by silica gel column chromatography to provide 6-bromo-1,3-dihydroisobenzofuran-1-ol (145, 530 mg, 96%) as yellow oil.
後処理
- customat −78° C.
- customThe resulting mixture was quenched with sat. Na2SO4
- temperatureto warm to room temperature
- additionTo the mixture was added anhydrous Na2SO4
- stirringthe mixture was stirred for 12 h
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude was purified by silica gel column chromatography
出典と根拠
- ORDレコード
- ord-5cd40f188d72430b94f3661e01c0cb50
- 出典データセット
- uspto-grants-2015_05
- 特許番号
- US09034921B2
反応ノート
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