Tetrahydrofuran → 3-Chlorobenzyl alcohol
반응식
[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]참가 물질
반응물 5
생성물 2
반응 조건
- 온도
- -78 °C
실험 절차
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).
후처리
- 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)
출처 및 근거
- ORD 기록
- ord-13922c5d96384ed8b54f960f33316fb8
- 출처 데이터셋
- uspto-grants-2003_02
- 특허 번호
- US06515011B2
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