反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[C:20]([CH3:21])=[C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:30])[CH:17]=2)[CH:12]=1)=O.Cl>O1CCCC1>[CH2:23]([O:22][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:30])[CH:17]=2)[CH:12]=[C:11]([CH2:9][OH:8])[C:20]=1[CH3:21])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1参加物
反応条件
- 温度
- 60 °C
実験手順
To the slurry of lithium aluminum hydride (1.8 g, 47.5 mmol) in tetrahydrofuran (50 mL) was added a solution of 4-benzyloxy-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl ester (10 g, 30.8 mmol) in tetrahydrofuran (50 mL) at 0° C. under a nitrogen atmosphere. After being heated at 60° C. for 2 hours, the resulting mixture was cooled to 0° C. and treated with 1 N hydrochloric acid to quench the reaction. The aqueous layer was extracted with diethyl ether (100 mL×5). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give (4-benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanol (8.4 g, 92%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.84 (dd, J=5.6, 9.2 Hz, 1H), 7.70 (dd, J=2.4, 10.0 Hz, 1H), 7.69 (s, 1H), 7.40-7.50 (m, 5H), 7.24 (td, J=2.4, 8.4 Hz, 1H), 4.99 (s, 2H), 4.87 (s, 2H), 2.47 (s, 3H).
後処理
- temperaturethe resulting mixture was cooled to 0° C.
- customto quench
- customthe reaction
- extractionThe aqueous layer was extracted with diethyl ether (100 mL×5)
- dry with materialThe combined organic layers were dried over sodium sulfate
- concentrationconcentrated in vacuo
出典と根拠
- ORDレコード
- ord-dc0c211618114f9491c6c9951f2a8617
- 出典データセット
- uspto-grants-2014_02
- 特許番号
- US08642629B2
関連ノート
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