Ammonium Chloride → 4-{3-Chloro-4-[2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-ethyl]-phenoxy}-benzonitrile

HRID 1095901노트

반응식

HRID 1095901 반응식
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH3:13])[CH:8]=1.[Cl:14][C:15]1[CH:16]=[C:17]([CH:27]=[CH:28][C:29]=1[CH:30]([CH3:33])[CH:31]=[O:32])[O:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1.[NH4+].[Cl-]>CCCCCC.C1COCC1>[Cl:14][C:15]1[CH:16]=[C:17]([CH:27]=[CH:28][C:29]=1[CH:30]([CH3:33])[CH:31]([OH:32])[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH3:13])[CH:8]=1)[O:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 27628354-Bromo-2-methylpyridineHCID 866459484-[3-Chloro-4-(1-methyl-2-oxo-ethyl)-phenoxy]-benzonitrileHCID 178418339Butyllithium

생성물 1

HCID 666990954-{3-Chloro-4-[2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-ethyl]-phenoxy}-benzonitrile

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

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온도
0 °C

실험 절차

A 1.6 M solution of n-BuLi in hexane (1.05 ml) was added to 4-bromo-2-methylpyridin (CAS Reg. No. 22282-99-1, 289 mg) in THF (5 ml) at −78° C. The deep red solution was stirred for 10 min. A solution of 4-[3-chloro-4-(1-methyl-2-oxo-ethyl)-phenoxy]-benzonitrile (400 mg) in THF (5 ml) was added at −78° C. The mixture was allowed to warm to 0° C. and stirred for 15 min at that temperature. Saturated aqueous NH4Cl solution was added and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2) to give the title compound (200 mg) as a light yellow solid. MS (m/e)=379.2 [M+H+].

후처리

  1. customat −78° C
  2. stirringstirred for 15 min at that temperature
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated to an oil
  6. customThe residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2)

출처 및 근거

ORD 기록
ord-983d7a252dbc4b11ba07c243f588774c
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138189B2

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