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

HRID 342509

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HRID 342509 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
40 °C

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-86d8a7d930f8469f9f096ad4edc162e3
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859020

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