3-Methoxybenzaldehyde → 2-Chloro-alpha-(3-methoxyphenyl)-3-pyridinemethanol

HRID 65535

반응식

HRID 65535 반응식
C([Li])CCC.Br[C:7]1[C:8]([Cl:13])=[N:9][CH:10]=[CH:11][CH:12]=1.ClC1C([Li])=CC=CN=1.[CH:22](=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1>CCCCCC.CCOCC.O>[Cl:13][C:8]1[C:7]([CH:22]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=2)[OH:31])=[CH:12][CH:11]=[CH:10][N:9]=1

참가 물질

8

반응물 4

HCID 115693-MethoxybenzaldehydeHCID 6933243-Bromo-2-chloropyridineHCID 178418339ButyllithiumHCID 178506730HCID 178506730, 화합물

생성물 1

HCID 201457332-Chloro-alpha-(3-methoxyphenyl)-3-pyridinemethanol수율 59.8%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매2회HCID 8058Hexane용매

실험 절차

71.5 ml of a 2.1N solution of n-butyllithium in hexane are added to 19.2 g 3-bromo-2-chloropyridine (obtained according to J. D. Cook et. al. J. Chem. Soc., Section C, 1969 1973-8) in 300 ml anhydrous ether at -60° C. and under a static nitrogen atmosphere. To this freshly prepared solution of 2-chloro-3-pyridyllithium, a solution of m-anisaldehyde (13.6 g) in 100 ml anhydrous ether is added dropwise. The reaction mixture is stirred for 1 hr. at -60° C. and then is added to ice:water. The organic phase is separated and the aqueous phase is extracted with ether. The combined organic solutions are washed with water, dried (MgSO4) and solvent evaporated. The crude oil is chromatographed over SiO2 and eluted with chloroform, obtaining 14.9 g of title product as an oil which spontaneously crystallises. Recrystallisation from methanol: water affords pure product, m.p. 114°-5° C.; Cl 14.65 (14.20).

후처리

  1. additionat -60° C. and then is added to ice
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted with ether
  4. washThe combined organic solutions are washed with water
  5. dry with materialdried (MgSO4) and solvent
  6. customevaporated
  7. customThe crude oil is chromatographed over SiO2
  8. washeluted with chloroform

출처 및 근거

ORD 기록
ord-c596dab32d0148ffad05acd071cc1af8
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04614833

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