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

HRID 659738

反応式

HRID 659738 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ee884524aae24f788390cbf66120db83
出典データセット
uspto-grants-2011_12
特許番号
US08080669B2

関連ノート

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