Sodium Bicarbonate → (E)-5-chloro-alpha-[2-(4-chlorophenyl)ethenyl]-2-methoxy-3-pyridinemethanol

HRID 280188ノート

反応式

HRID 280188 の反応式
Br[C:2]1[C:3]([O:9][CH3:10])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.C([Li])CCC.CCCCCC.[Cl:22][C:23]1[CH:32]=[CH:31][C:26]([CH:27]=[CH:28][CH:29]=[O:30])=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+]>CCOCC>[Cl:8][C:6]1[CH:7]=[C:2]([CH:29](/[CH:28]=[CH:27]/[C:26]2[CH:25]=[CH:24][C:23]([Cl:22])=[CH:32][CH:31]=2)[OH:30])[C:3]([O:9][CH3:10])=[N:4][CH:5]=1

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 3794977p-ChlorocinnamaldehydeHCID 135677513-Bromo-5-chloro-2-methoxypyridineHCID 178418244HCID 178418244、化合物

生成物 1

HCID 13567753(E)-5-chloro-alpha-[2-(4-chlorophenyl)ethenyl]-2-methoxy-3-pyridinemethanol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A solution of 4.0 g of 3-bromo-5-chloro-2-methoxypyridine in 75 ml of anhydrous ether was cooled to -70° C. under nitrogen. The resulting slurry was stirred rapidly and there was added 12.0 ml of 1.65M n-butyllithium/hexane dropwise over a period of about 5 minutes while keeping the temperature below -70° C. The reaction mixture became homogeneous and, after 15 minutes, a solution of 3.0 g of 4-chlorocinnamaldehyde in 35 ml of ether was added dropwise while keeping the temperature below -60° C. The cold mixture was then poured into aqueous saturated sodium bicarbonate solution and the resulting mixture was extracted with ether. The ether layer was washed with aqueous saturated sodium chloride solution, dried over potassium carbonate and concentrated under reduced pressure to give a white solid. This solid was recrystallized from a mixture of ethyl acetate/hexane to give (E)-5-chloro-α-[2-(4-chlorophenyl)ethenyl]-2-methoxy-3-pyridinemethanol as white needles melting at about 135°-139.5° C.

後処理

  1. customthe temperature below -70° C
  2. customthe temperature below -60° C
  3. extractionthe resulting mixture was extracted with ether
  4. washThe ether layer was washed with aqueous saturated sodium chloride solution
  5. dry with materialdried over potassium carbonate
  6. concentrationconcentrated under reduced pressure
  7. customto give a white solid
  8. customThis solid was recrystallized from a mixture of ethyl acetate/hexane

出典と根拠

ORDレコード
ord-8fcb9ecd3dda438e8bfbd3e0f54d3208
出典データセット
uspto-grants-1986_05
特許番号
US04588733

反応ノート

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