Acetic Acid → Methyl 2-isocyano-2-(2-thienylmethyl)butyrate

HRID 1722734ノート

反応式

HRID 1722734 の反応式
CC(C)([O-])C.[K+].[N+:7]([CH:9]([CH2:14][CH3:15])[C:10]([O:12][CH3:13])=[O:11])#[C-:8].Br[CH2:17][C:18]1[S:19][CH:20]=[CH:21][CH:22]=1.C(O)(=O)C>O1CCCC1>[N+:7]([C:9]([CH2:17][C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)([CH2:14][CH3:15])[C:10]([O:12][CH3:13])=[O:11])#[C-:8]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 118299782-(Bromomethyl)thiopheneHCID 16754012Methyl 2-isocyanobutyrateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 20027427Methyl 2-isocyano-2-(2-thienylmethyl)butyrate収率 88.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-30 °C

実験手順

A suspension of potassium tert.-butoxide (5.5 g) in tetrahydrofuran (50 ml) is cooled to -30° C., and a solution of methyl 2-isocyanobutyrate (5.5 g) in tetrahydrofuran (10 ml) is added dropwise to the suspension at -30° C. The mixture is stirred at the same temperature for 30 minutes and a solution of 2-bromomethylthiophene (6.9 g) in tetrahydrafuran (10 ml) is added dropwise to the mixture. The mixture is stirred at room temperature for 4 hours, adjusted to pH 7 with acetic acid and then concentrated under reduced pressure to remove solvent. The residue is dissolved in a mixture of ethyl acetate and water and the organic layer is collected therefrom. The organic layer is washed with an aqueous saturated sodium chloride solution, dried and concentrated to remove solvent. The residue is distilled under reduced pressure, whereby methyl 2-isocyano-2-(2-thienylmethyl)butyrate (7.7 g) is obtained as pale yellow oil.

後処理

  1. stirringThe mixture is stirred at room temperature for 4 hours
  2. concentrationconcentrated under reduced pressure
  3. customto remove solvent
  4. dissolutionThe residue is dissolved in a mixture of ethyl acetate and water
  5. customthe organic layer is collected
  6. washThe organic layer is washed with an aqueous saturated sodium chloride solution
  7. customdried
  8. concentrationconcentrated
  9. customto remove solvent
  10. distillationThe residue is distilled under reduced pressure

出典と根拠

ORDレコード
ord-759e756f67714c06833db969e245f1ad
出典データセット
uspto-grants-1989_08
特許番号
US04857543

反応ノート

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