Tetrahydrofuran → 3-Chlorobenzyl alcohol
反応式
[Cl:1][C:2]1[CH:9]=CC(I)=C[C:3]=1CO.[H-].[Na+].C([Li])CCC.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[CH:27][C:28]([F:31])([F:30])[F:29])=[CH:22][CH:21]=1.[CH2:32]1[CH2:36][O:35][CH2:34][CH2:33]1>>[Cl:1][C:2]1[CH:9]=[CH:34][C:33]([CH:27]([NH:26][C:23]2[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)[C:28]([F:29])([F:30])[F:31])=[C:32]([CH2:36][OH:35])[CH:3]=1.[Cl:1][C:2]1[CH:3]=[C:32]([CH:33]=[CH:34][CH:9]=1)[CH2:36][OH:35]参加物
反応物 5
生成物 2
反応条件
- 温度
- -78 °C
実験手順
A solution of 2-chloro-5-iodobenzyl alcohol (0.537 g, 2.0 mmol) in THF (10 mL) was added to sodium hydride (88 mg of a 60% dispersion in mineral oil, 2.2 mmol) at 0° C. with stirring under nitrogen. After 5 min the mixture was cooled to −78° C. and n-butyl-lithium (2.5 M in hexanes, 1.66 mL, 4.15 mmol) was added over 6 min. After a further 5 min a solution of N-(4-methoxyphenyl)-N-(-2,2,2-trifluoroethylidene)amine (0.406 g, 2.0 mmol) in THF (2 mL) was added over 5 min. After a further 5 min the reaction was quenched with saturated ammonium chloride solution and the mixture was warmed to ambient temperature and partitioned between ethyl acetate and brine. The organic layer was dried (Na2SO4) and evaporated to a gum which was purified by chromatography on silica (eluting with 2% methanol/chloroform) to give N-{1-[4-chloro-2-(hydroxymethyl)phenyl]-2,2,2-trifluoroethyl}-N-(4-methoxyphenyl)amine as a 1:1.7 mixture with 3-chlorobenzyl alcohol (0.38 g) as a gum: MS 346.4 (M+1).
後処理
- customAfter a further 5 min the reaction was quenched with saturated ammonium chloride solution
- temperaturethe mixture was warmed to ambient temperature
- custompartitioned between ethyl acetate and brine
- dry with materialThe organic layer was dried (Na2SO4)
- customevaporated to a gum which
- customwas purified by chromatography on silica (eluting with 2% methanol/chloroform)
出典と根拠
- ORDレコード
- ord-13922c5d96384ed8b54f960f33316fb8
- 出典データセット
- uspto-grants-2003_02
- 特許番号
- US06515011B2
反応ノート
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