1-(diethoxymethyl)-1H-imidazole → Rac-(2-chloro-6-ethyl-phenyl)-(1h-imidazol-2-yl)-methanol

HRID 254547

반응식

HRID 254547 반응식
C(OC(OCC)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)C.C([Li])CCC.[Cl:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][CH3:28])[C:20]=1[CH:21]=[O:22]>O1CCCC1.CCCCCC>[Cl:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][CH3:28])[C:20]=1[CH:21]([C:6]1[NH:5][CH:9]=[CH:8][N:7]=1)[OH:22]

참가 물질

6

반응물 3

HCID 38495351-(diethoxymethyl)-1H-imidazoleHCID 226137462-Chloro-6-ethylbenzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 58951722Rac-(2-chloro-6-ethyl-phenyl)-(1h-imidazol-2-yl)-methanol수율 96%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
0 °C

실험 절차

To a solution of 1.60 ml (9.79 mmol) 1-(diethoxymethyl)imidazole in 6 ml tetrahydrofuran at −78° C. was added dropwise 6.67 ml (10.7 mmol) of a 1.6 M solution of n-butyllithium in hexane. The resulting solution of 2-(1-diethoxymethyl-1H-imidazol-2-yl)-lithium was stirred at −78° C., and then added dropwise to a solution of 1.50 g (8.90 mmol) 2-chloro-6-ethyl-benzaldehyde in 6 ml tetrahydrofuran at 0° C. The reaction mixture was then stirred at 0° C. for 30 min and at room temperature for 1 h, before being quenched by dropwise addition of 1 M aqueous hydrochloric acid. The mixture was made basic by addition of aqueous sodium bicarbonbate solution and diluted with ethyl acetate. The phases were separated and the organic phase was washed with saturated brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 2.02 g (96%) of the title compound as a yellow oil which was used in the next step without further purification.

후처리

  1. custombefore being quenched by dropwise addition of 1 M aqueous hydrochloric acid
  2. additionThe mixture was made basic by addition of aqueous sodium bicarbonbate solution
  3. additiondiluted with ethyl acetate
  4. customThe phases were separated
  5. washthe organic phase was washed with saturated brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-fb0ff5af83ff4a84b6de1cbebac26022
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875645B2

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