Ethyl Acetate → Ethyl 2-(4-cyanopyridin-3-YL)acetate

HRID 1844013노트

반응식

HRID 1844013 반응식
[C-:1]#[N:2].[K+].C(I)C.[CH2:7]([O:9][C:10](=[O:19])[CH2:11][C:12]1[CH:13]=[N+:14]([O-])[CH:15]=[CH:16][CH:17]=1)[CH3:8].C(OCC)(=O)C>O.C(O)C.O.CCCCCC>[C:1]([C:17]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[CH2:11][C:10]([O:9][CH2:7][CH3:8])=[O:19])#[N:2]

참가 물질

7

반응물 3

HCID 8857Ethyl AcetateHCID 9032Potassium CyanideHCID 899646883-(2-Ethoxy-2-oxoethyl)pyridine-1-oxide ethyl iodide

생성물 1

HCID 12251980Ethyl 2-(4-cyanopyridin-3-YL)acetate수율 80.3%

시약·촉매·용매 3

HCID 962Water용매HCID 8058Hexane용매HCID 19096565Water ethanol용매

실험 절차

KCN (2.64 g, 31.44 mmol) in water (8 mL) was added drop wise over a period of 20 minutes to a solution of 3-(2-ethoxy-2-oxoethyl)pyridine-1-oxide ethyl iodide (I-67b: 5.3 g, 15.72 mmol) in ethanol-water (7:3 ratio, 30 mL) at 50° C. and heating was further continued for another 30 minutes. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mass was quenched using ice and extracted using DCM. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3) afforded 2.4 g of the product.

후처리

  1. temperatureheating
  2. customThe reaction mass was quenched
  3. extractionextracted
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude product
  7. customPurification by column chromatography on silica gel (1% methanol in CHCl3)

출처 및 근거

ORD 기록
ord-67a9ff7569df4780a3b76a3cd61c1846
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946260B2

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