(E)-1,3-Dichloropropene → (E)-2-(1-Methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methyl-6-(3-chloroprop-2-enyloxy)pyridine

HRID 23318

반응식

HRID 23318 반응식
[OH:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[CH:5]=[C:4]([CH3:19])[CH:3]=1.[H-].[Na+].[Cl:22]/[CH:23]=[CH:24]/[CH2:25]Cl>C(#N)C.CN(C=O)C.CCCCC.C(OCC)(=O)C>[CH3:14][N:13]1[C:9]([O:8][C:6]2[CH:5]=[C:4]([CH3:19])[CH:3]=[C:2]([O:1][CH2:25]/[CH:24]=[CH:23]/[Cl:22])[N:7]=2)=[CH:10][C:11]([C:15]([F:18])([F:17])[F:16])=[N:12]1

참가 물질

7

반응물 3

HCID 24726(E)-1,3-DichloropropeneHCID 24758Sodium hydride2회HCID 178429419HCID 178429419, 화합물

생성물 1

HCID 15477174(E)-2-(1-Methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methyl-6-(3-chloroprop-2-enyloxy)pyridine수율 52.3%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매HCID 22335286Ethyl acetate pentane용매

실험 절차

A mixture of 6-hydroxy-2-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methylpyridine (0.9 g, 3.3 mmol) and NaH (60% in oil, 0.16 g, 4 mmol) in acetonitrile (20 ml) and DMF (1 ml) is stirred for 10 min at ambient temperature and (E)-1,3-dichloropropene (0.4 g, 3.6 mmol) is added. After stirring for 60 h at ambient temperature, the remaining NaH is deactivated and the resulting mixture is diluted with pentane/ethyl acetate (by volume ration 1/1) and filtered through a bed of silica gel. The filtrate is washed with water. The organic layer is dried with anhydrous magnesium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v) yields the title compound (0.6 g, 52% yield) as an colorless oil.

후처리

  1. stirringAfter stirring for 60 h at ambient temperature
  2. filtrationfiltered through a bed of silica gel
  3. washThe filtrate is washed with water
  4. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customPurification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v)

출처 및 근거

ORD 기록
ord-1a51b45be5a940eea36ea661e6865feb
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852673B2

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