Ammonium Chloride → alpha-(1-Ethoxymethyl-5-pyrazolyl)-2,3-dichloro-4-methoxy-benzylalcohol

HRID 1721935

반응식

HRID 1721935 반응식
C([Li])CCC.[CH2:6]([O:8][CH2:9][N:10]1[CH:14]=[CH:13][CH:12]=[N:11]1)[CH3:7].[Cl:15][C:16]1[C:23]([Cl:24])=[C:22]([O:25][CH3:26])[CH:21]=[CH:20][C:17]=1[CH:18]=[O:19].[Cl-].[NH4+]>CCCCCC.O1CCCC1.O>[CH2:6]([O:8][CH2:9][N:10]1[C:14]([CH:18]([OH:19])[C:17]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[C:23]([Cl:24])[C:16]=2[Cl:15])=[CH:13][CH:12]=[N:11]1)[CH3:7]

참가 물질

8

반응물 4

HCID 25517Ammonium ChlorideHCID 130156892,3-Dichloro-4-methoxybenzaldehydeHCID 157143991-(ethoxymethyl)-1H-pyrazoleHCID 178418339Butyllithium

생성물 1

HCID 14622784alpha-(1-Ethoxymethyl-5-pyrazolyl)-2,3-dichloro-4-methoxy-benzylalcohol수율 81.5%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

4.13 ml of 1.6M n-butyl lithium in hexane are added dropwise to a tetrahydrfuran solution of 0.76 g of 1-ethoxymethylpyrazole at -60° C. under argon gas atmosphere. the mixture is stirred at -63° to -50° C. for 1 hour. A solution of 1.23 g of 2,3-dichloro-4-methoxybenzaldehyde in tetrahydrofuran is added to the mixture, and the mixture is stirred at -50° C. to room temperature for 1 hour. An aqueous saturated ammonium chloride solution and water are added to the mixture under ice-cooling and the mixture is concentrated to remove tetrahydrofuran. The residual aqueous layer is extracted with ethyl acetate and the extract is washed with water, dried and evaporated to give colorless crystals, which are then washed with isopropyl ether and dried to give 1.62 g of α-(1-ethoxymethyl-5-pyrazolyl)-2,3-dichloro-4-methoxy-benzylalcohol.

후처리

  1. stirringthe mixture is stirred at -50° C. to room temperature for 1 hour
  2. temperaturecooling
  3. concentrationthe mixture is concentrated
  4. customto remove tetrahydrofuran
  5. extractionThe residual aqueous layer is extracted with ethyl acetate
  6. washthe extract is washed with water
  7. customdried
  8. customevaporated
  9. customto give colorless crystals, which
  10. washare then washed with isopropyl ether
  11. customdried

출처 및 근거

ORD 기록
ord-80735a99aa4444a89e563646f5f0c8f6
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04853404

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