Citric Acid → 5-Bromo-2-chloro-1-(4-methoxycarbonyl-5-oxazolylmethyl)benzene

HRID 1625887ノート

反応式

HRID 1625887 の反応式
CC(C)([O-])C.[K+].[N+:7]([CH2:9][C:10]([O:12][CH3:13])=[O:11])#[C-:8].[Br:14][C:15]1[CH:16]=[CH:17][C:18]([Cl:25])=[C:19]([CH2:21][C:22](Cl)=[O:23])[CH:20]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([Cl:25])=[C:19]([CH2:21][C:22]2[O:23][CH:8]=[N:7][C:9]=2[C:10]([O:12][CH3:13])=[O:11])[CH:20]=1

参加物

6

反応物 4

HCID 311Citric AcidHCID 547815Methyl isocyanoacetateHCID 23665647Potassium tert-butoxideHCID 861877695-Bromo-2-chlorophenylacetyl chloride

生成物 1

HCID 666081825-Bromo-2-chloro-1-(4-methoxycarbonyl-5-oxazolylmethyl)benzene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of potassium t-butoxide (1.35 g) in tetrahydrofuran (20 ml) was cooled to 0° C., and thereto was added methyl isocyanoacetate (1.33 ml). Then, a solution of the above 5-bromo-2-chlorophenylacetyl chloride in tetrahydrofuran (20 ml) was added thereto, and the mixture was stirred at 0° C. for 2 hours, and then at room temperature overnight. The mixture was cooled again to 0° C. 10% aqueous citric acid solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give 5-bromo-2-chloro-1-(4-methoxycarbonyl-5-oxazolylmethyl)benzene (1.12 g) as a yellow solid. APCI-Mass m/Z 330/332 (M+H).

後処理

  1. customat room temperature
  2. customovernight
  3. temperatureThe mixture was cooled again to 0° C
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-ce431aa5c3394967838b3b93b3155dac
出典データセット
uspto-grants-2014_07
特許番号
US08785403B2

反応ノート

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