Sodium hydride → 2-Chloro-3-(2-methyl-1-propen-3-yl)-4-iodo-6-(1-hydroxyethyl)-pyridine

HRID 1637775

반응식

HRID 1637775 반응식
[Cl:1][C:2]1[C:7](O)=[C:6]([I:9])[CH:5]=[C:4]([CH:10]([OH:12])[CH3:11])[N:3]=1.[H-].[Na+].[CH3:15][C:16]([CH2:18]Br)=[CH2:17]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([CH2:17][C:16]([CH3:18])=[CH2:15])=[C:6]([I:9])[CH:5]=[C:4]([CH:10]([OH:12])[CH3:11])[N:3]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 3577853-Bromo-2-methyl-1-propeneHCID 107092992-Chloro-3-hydroxy-4-iodo-6-(1-hydroxyethyl)-pyridine

생성물 1

HCID 187996482-Chloro-3-(2-methyl-1-propen-3-yl)-4-iodo-6-(1-hydroxyethyl)-pyridine수율 77.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2-chloro-3-hydroxy-4-iodo-6-(1-hydroxyethyl)-pyridine (4.49 g, 15 mmol) in 25 mL of N,N-dimethylformamide at 0° C. is treated with 600 mg (60% in oil, 15 mmol) of sodium hydride and stirred at room temperature for 1 h. The reaction is treated with 1.7 mL (16.5 mmol) of 2-methyl-3-bromopropene and stirred for 2 h. The mixture is diluted with 150 mL of ethyl acetate and washed with 4×50 mL of 1:1 50% saturated sodium chloride/sodium bicarbonate, and dried over potassium carbonate. The crude material is chromatographed over 150 g of silica gel (230-400 mesh), eluting with 25% ethyl acetate/hexanes to give 3.94 g (74%) of 2-chloro-3-(2-methyl-1-propen-3-yl)-4-iodo-6-(1-hydroxyethyl)-pyridine.

후처리

  1. stirringstirred for 2 h
  2. washwashed with 4×50 mL of 1:1 50% saturated sodium chloride/sodium bicarbonate
  3. dry with materialdried over potassium carbonate
  4. customThe crude material is chromatographed over 150 g of silica gel (230-400 mesh)
  5. washeluting with 25% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-c6d1af5460af4aa598efc430bbc2f92f
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06043248

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