Thionyl Chloride → Methyl 5-cyano-2-methoxybenzoate

HRID 1601440

반응식

HRID 1601440 반응식
CO[C:3]1C=C[C:11]([CH:14]=[O:15])=[CH:10][C:4]=1[C:5](=[N:8]O)OC.S(Cl)(Cl)=O.[C:20]([O:23][CH2:24]C)(=[O:22])[CH3:21].[CH3:26]CCCCC>ClCCl>[CH3:26][O:15][C:14]1[CH:11]=[CH:10][C:4]([C:5]#[N:8])=[CH:3][C:21]=1[C:20]([O:23][CH3:24])=[O:22]

참가 물질

5

반응물 3

HCID 24386Thionyl ChlorideHCID 21226206Ethyl acetate hexaneHCID 86583897Methyl 2-methoxy-5-formylbenzoate oxime

생성물 1

HCID 18464789Methyl 5-cyano-2-methoxybenzoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Combine methyl 2-methoxy-5-formylbenzoate oxime (3.5 g, 16.7 mmol) in dichloromethane (75 mL) and cool in an ice-bath. Add dropwise thionyl chloride (2.0 mL, 27.2 mmol). after 20 minutes, dilute the reaction mixture with dichloromethane and extract with a saturated aqueous solution of sodium bicarbonate and then brine. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1/1 ethyl acetate/hexane to give methyl 2-methoxy-5-cyanobenzoate.

후처리

  1. extractionextract with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialDry the organic layer over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customto give a residue

출처 및 근거

ORD 기록
ord-cc6721623e6a4b49994f211618456cec
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05977139

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