Diethyl Ether → 3-tert-Butoxy-5-fluoropyrazine-2-carboxaldehyde

HRID 606191노트

반응식

HRID 606191 반응식
[C:1]([O:5][C:6]1[C:7]([CH:13]=[O:14])=[N:8][CH:9]=[C:10](Cl)[N:11]=1)([CH3:4])([CH3:3])[CH3:2].[F-:15].[K+].C1OCCOCCOCCOCCOCCOC1.C(OCC)C>C(#N)C.[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6]1[C:7]([CH:13]=[O:14])=[N:8][CH:9]=[C:10]([F:15])[N:11]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 222482023-Tert-butoxy-5-chloropyrazine-2-carboxaldehyde

생성물 1

HCID 222482523-tert-Butoxy-5-fluoropyrazine-2-carboxaldehyde수율 3.4%

시약·촉매·용매 2

HCID 2724163Tetraphenylphosphonium Bromide촉매HCID 6342Acetonitrile용매

실험 절차

After dissolving 5.86 g of the crude 3-tert-butoxy-5-chloropyrazine-2-carboxaldehyde in 55 ml of acetonitrile, 4.77 g of potassium fluoride, 1.13 g of tetraphenylphosphonium bromide and 0.71 g of 18-crown-6 were added and the mixture was heated to reflux for 4 hours. Diethyl ether was added to the reaction mixture, the insoluble portion was filtered out, and the filtrate was distilled off under reduced pressure. Ethyl acetate was added to the residue, the insoluble portion was filtered out, and the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: toluene/ethyl acetate) to obtain the title compound (183 mg, 3% yield).

후처리

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 4 hours
  4. filtrationthe insoluble portion was filtered out
  5. distillationthe filtrate was distilled off under reduced pressure
  6. additionEthyl acetate was added to the residue
  7. filtrationthe insoluble portion was filtered out
  8. distillationthe filtrate was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (solvent: toluene/ethyl acetate)

출처 및 근거

ORD 기록
ord-770ff0fc104f4f0d81c830c87f9b527d
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915274B2

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