反応式
[CH3:1][O:2][C:3]([C:5]1[C:14]([CH3:15])=[C:13]([OH:16])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:17])[CH:11]=2)[CH:6]=1)=[O:4].C([O-])([O-])=O.[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].O>[CH3:1][O:2][C:3]([C:5]1[C:14]([CH3:15])=[C:13]([O:16][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:17])[CH:11]=2)[CH:6]=1)=[O:4]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 3
実験手順
To a solution of 6-fluoro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acid methyl ester (21.7 g, 92.7 mmol) in dry DMF (250 mL) was added K2CO3 (17.9 g, 130 mmol), benzyl bromide (13 mL, 111 mmol) and Bu4NI (0.250 g) at room temperature under nitrogen. The reaction mixture was stirred for 3 hours at room temperature. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with water, brine, dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified using silica gel column chromatography (2-5% ethyl acetate-hexane) to yield 4-benzyloxy-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl ester (25.4 g, 84%) as an off-white solid. MS cald. for C20H18FO3 [(M+H)+]: 325, obsd. 325.1.
後処理
- extractionextracted with ethyl acetate
- washThe combined organic extracts were washed with water, brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customto give the crude product, which
- customwas purified
出典と根拠
- ORDレコード
- ord-6cc90fddf5d7480f80576bcf1c85d8e0
- 出典データセット
- uspto-grants-2013_06
- 特許番号
- US08470884B2
関連ノート
読み込み中…