Thionyl Chloride → Ethyl 6-(chloromethyl)nicotinate

HRID 1030513노트

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HRID 1030513 반응식
O[CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]=1.S(Cl)([Cl:16])=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:16][CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]=1

참가 물질

5

반응물 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 15045504Ethyl 6-(hydroxymethyl)pyridine-3-carboxylate

생성물 1

HCID 15045505Ethyl 6-(chloromethyl)nicotinate수율 90.9%

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
0 °C

실험 절차

A solution of 10.5 g of ethyl 6-hydroxymethylnicotinate in chloroform (100 ml) was cooled to 0° C., and 8.28 g of thionyl chloride was added dropwise to the solution. The mixture was stirred at 0° C. for 2 hours, an aqueous solution of sodium hydrogencarbonate was added, and the mixture was extracted with dichloromethane. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexene/ethyl acetate=6/1) to obtain 10.52 g of ethyl 6-chloromethylnicotinate.

후처리

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (n-hexene/ethyl acetate=6/1)

출처 및 근거

ORD 기록
ord-c261d04a19c4419686e6e6b2aa1e8fca
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05106859

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