Heptane → 4-(1,3-Oxazol-5-yl)benzonitrile

HRID 659738

반응식

HRID 659738 반응식
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=[O:2].S([CH2:21][N+:22]#[C-:23])(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+].CCCCCCC>CO>[O:2]1[C:1]([C:3]2[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=2)=[CH:23][N:22]=[CH:21]1

참가 물질

6

반응물 4

HCID 8900HeptaneHCID 11430Potassium CarbonateHCID 660424-CyanobenzaldehydeHCID 161915Tosylmethyl isocyanide

생성물 1

HCID 27772714-(1,3-Oxazol-5-yl)benzonitrile수율 97%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 4-Formyl-benzonitrile (5 g, 38.17 mmol) and tosylmethyl isocyanide (TosMIC) (from Aldrich, 8.33 g, 42 mmol) in MeOH (200 mL) was added K2CO3 (6.85 g, 49.62 mmol) and the mixture was stirred at reflux for 1 h. The solvent was then evaporated and saturated aqueous NaHCO3 was added. The resultant suspension was extracted with dichloromethane (3×100 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous MgSO4 and concentrated to leave a yellow solid. Trituration with heptane afforded a solid that was collected by filtration and dried under vacuum to give the title compound (6.3 g, 97%). m.p.=140° C.

후처리

  1. temperatureat reflux for 1 h
  2. customThe solvent was then evaporated
  3. additionsaturated aqueous NaHCO3 was added
  4. extractionThe resultant suspension was extracted with dichloromethane (3×100 mL)
  5. washThe combined organic layers were washed with brine (30 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated
  8. customto leave a yellow solid
  9. filtrationthat was collected by filtration
  10. customdried under vacuum

출처 및 근거

ORD 기록
ord-ee884524aae24f788390cbf66120db83
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080669B2

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