Ammonium Chloride → (5-Chloro-6-methoxypyridin-2-yl)[4-(methylsulfanyl)phenyl]methanol

HRID 70497

反応式

HRID 70497 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1.[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH:24]=[O:25])=[N:20][C:21]=1[O:22][CH3:23].[Cl-].[NH4+]>O1CCCC1>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH:24]([C:7]2[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=2)[OH:25])=[N:20][C:21]=1[O:22][CH3:23]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 660374-BromothioanisoleHCID 584528465-Chloro-6-methoxypicolinaldehydeHCID 178418339Butyllithium

生成物 1

HCID 67396108(5-Chloro-6-methoxypyridin-2-yl)[4-(methylsulfanyl)phenyl]methanol収率 72.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

n-Butyllithium (2.64 M, 2.9 mL) was added to a solution of 4-bromothioanisole (1.61 g) in tetrahydrofuran (20 mL) at −78° C. in a nitrogen atmosphere, and the mixture was stirred at the same temperature for 30 minutes. A solution of 5-chloro-6-methoxypyridine-2-carbaldehyde (1.14 g) in tetrahydrofuran (10 mL) was added to the reaction solution, followed by stirring for one hour. The reaction solution was poured into a saturated ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→4:1) to give (5-chloro-6-methoxypyridin-2-yl)[4-(methylsulfanyl)phenyl]methanol as a pale yellow oil (1.42 g).

後処理

  1. stirringby stirring for one hour
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationafter which the filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→4:1)

出典と根拠

ORDレコード
ord-f806ee9f51c84a7e8397092246675d0c
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

関連ノート

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