Sodium hydride → 4-[2-(4-Chlorophenyl)ethoxy]-5-methoxy-6-chloropyrimidine

HRID 342509

反応式

HRID 342509 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[Cl:15][C:16]1[C:21]([O:22][CH3:23])=[C:20](Cl)[N:19]=[CH:18][N:17]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:20]2[C:21]([O:22][CH3:23])=[C:16]([Cl:15])[N:17]=[CH:18][N:19]=2)=[CH:4][CH:3]=1

参加物

7

反応物 5

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 74647p-Chlorophenethylic alcoholHCID 787204,6-Dichloro-5-methoxypyrimidineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 544366424-[2-(4-Chlorophenyl)ethoxy]-5-methoxy-6-chloropyrimidine収率 88%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

2.40 g (15.2 mmol) of 2-(4-chlorophenyl)ethanol were added dropwise at 40° C. to a suspension of 680 mg (22.7 mmol) of sodium hydride (80% suspension in oil) in 40 ml of dry tetrahydrofuran, and the mixture was stirred until the evolution of hydrogen had ceased. The mixture was then allowed to cool to room temperature, whereupon 2.7 g (15.2 mmol) of 4,6-dichloro-5-methoxypyrimidine (Monatshefte Chem. 96, 1661 (1965) were added in portions. The mixture was stirred for 1 hour at room temperature and for 4 hours at 40° C. For work-up, the reaction mixture was poured into saturated ammonium chloride solution and extracted with diethyl ether. The combined organic phase was dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel using n-heptane/ethyl acetate (4:1). 4.0 g (88% of theory) of 4-[2-(4-chlorophenyl)ethoxy]-5-methoxy-6-chloropyrimidine was obtained in the form of a viscous oil which crystallized slowly upon drying (melting point 70°-71° C.).

後処理

  1. addition96, 1661 (1965) were added in portions
  2. extractionextracted with diethyl ether
  3. dry with materialThe combined organic phase was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-86d8a7d930f8469f9f096ad4edc162e3
出典データセット
uspto-grants-1999_01
特許番号
US05859020

関連ノート

読み込み中…