Chloroacetonitrile → 5,6-Dimethoxy-2,3-dihydrobenzofuran-2-carbonitrile

HRID 458521노트

반응식

HRID 458521 반응식
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[CH:4]=O.Cl[CH2:15][C:16]#[N:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:13][O:12][C:7]1[C:8]([O:10][CH3:11])=[CH:9][C:2]2[O:1][CH:15]([C:16]#[N:17])[CH2:4][C:3]=2[CH:6]=1

참가 물질

5

반응물 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 109869082-Hydroxy-4,5-dimethoxybenzaldehyde

생성물 1

HCID 184425025,6-Dimethoxy-2,3-dihydrobenzofuran-2-carbonitrile수율 51%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
165 °C

실험 절차

2-Hydroxy-4,5-dimethoxybenzaldehyde (25.5 g, 0.14 mol), chloroacetonitrile (12.4 g, 0.168 mol) and potassium carbonate (116 g, 0.84 mol) was dissolved in DMF (150 ml). The mixture was stirred for 10 minutes at 165° C. The solvent was concentrated under reduced pressure. The residue was separated in two parts, water was added and the first part was extracted with diethyl ether and the second part extracted with DCM. The second part was evaporated under reduced pressure and dissolved in ether and washed once with water. The organic layers was combined and evaporated under reduced pressure. The crystalline residue was washed with warm methanol (700 ml) and filtered. The residue was dissolved in 225 ml DCM and diethyl ether (450 ml) was added. The crystals formed was collected giving 14.6 g (51% yield) of product. Mp. 162° C.

후처리

  1. concentrationThe solvent was concentrated under reduced pressure
  2. customThe residue was separated in two parts, water
  3. additionwas added
  4. extractionthe first part was extracted with diethyl ether
  5. extractionthe second part extracted with DCM
  6. customThe second part was evaporated under reduced pressure
  7. dissolutiondissolved in ether
  8. washwashed once with water
  9. customevaporated under reduced pressure
  10. washThe crystalline residue was washed with warm methanol (700 ml)
  11. filtrationfiltered
  12. dissolutionThe residue was dissolved in 225 ml DCM
  13. additiondiethyl ether (450 ml) was added
  14. customThe crystals formed
  15. customwas collected

출처 및 근거

ORD 기록
ord-7901c477907046e8b02dae7628907b65
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192946B2

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