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

HRID 65535

反応式

HRID 65535 の反応式
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

参加物

8

反応物 4

HCID 115693-MethoxybenzaldehydeHCID 6933243-Bromo-2-chloropyridineHCID 178418339ButyllithiumHCID 178506730HCID 178506730、化合物

生成物 1

HCID 201457332-Chloro-alpha-(3-methoxyphenyl)-3-pyridinemethanol収率 59.8%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回HCID 8058Hexane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c596dab32d0148ffad05acd071cc1af8
出典データセット
uspto-grants-1986_09
特許番号
US04614833

関連ノート

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