4-Fluoroanisole → (2-Fluoro-5-methoxy-phenyl)-4-pyridylmethanol

HRID 273735

반응식

HRID 273735 반응식
C([Li])CCC.CN(C)CCN(C)CCN(C)C.[F:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1.[N:27]1[CH:32]=[CH:31][C:30]([CH:33]=[O:34])=[CH:29][CH:28]=1>C1COCC1>[F:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[CH:33]([C:30]1[CH:31]=[CH:32][N:27]=[CH:28][CH:29]=1)[OH:34]

참가 물질

6

반응물 4

HCID 99874-FluoroanisoleHCID 133894-PyridinecarboxaldehydeHCID 18196PentamethyldiethylenetriamineHCID 178418339Butyllithium

생성물 1

HCID 15839523(2-Fluoro-5-methoxy-phenyl)-4-pyridylmethanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-75 °C

실험 절차

Butyl lithium (47.5 ml of 2.22M solution, 105.6 mmole) was added slowly to a solution of pentamethyldiethylenetriamine (15 ml) and 4-fluoroanisole (12.61 g, 0.1 mole) in THF (150 ml) at -70° C. The solution was stirred for 2 hr at -75° C. and a solution of pyridine-4-aldehyde (9.55 ml, 0.1 mole) in THF was added at -75° C. The mixture was allowed to warm to 25° C. slowly and then quenched with ammonium chloride solution. The mixture was diluted with ethyl acetate and the organic layer was separated. The organic layer was washed with water and 3N hydrochloric acid. The acid washes were then basified with sodium hydroxide and extracted with ether and the ether solution concentrated in vacuo. The crude product was recrystallized from 80% ethanol to give (2-fluoro-5-methoxy-phenyl)-4-pyridylmethanol as a white powder (12.22 g+3.12 g second crop, 65.8% total yield).

후처리

  1. temperatureto warm to 25° C. slowly
  2. customquenched with ammonium chloride solution
  3. additionThe mixture was diluted with ethyl acetate
  4. customthe organic layer was separated
  5. washThe organic layer was washed with water and 3N hydrochloric acid
  6. extractionextracted with ether
  7. concentrationthe ether solution concentrated in vacuo
  8. customThe crude product was recrystallized from 80% ethanol
  9. customto give

출처 및 근거

ORD 기록
ord-9e5b4049d4ec4d8581fdf77a8058c374
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387593

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