Toluene → HCID 178500902、化合物

HRID 50102

反応式

HRID 50102 の反応式
[C:1]([CH2:6][C:7]([O:9][CH3:10])=[O:8])(=[O:5])[CH:2]([CH3:4])[CH3:3].[F:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.C1(C)C=CC=CC=1.[Sn](Cl)(Cl)(Cl)Cl>CCCCCC>[NH2:17][C:16](=[C:6]([C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[C:7]([O:9][CH3:10])=[O:8])[C:15]1[CH:18]=[CH:19][C:12]([F:11])=[CH:13][CH:14]=1

参加物

6

反応物 4

HCID 1140TolueneHCID 145174-FluorobenzonitrileHCID 24287Tin tetrachlorideHCID 2759969Methyl 4-methyl-3-oxopentanoate

生成物 1

HCID 178500902HCID 178500902、化合物収率 75.2%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
80 °C

実験手順

75.09 g of methyl isobutyrylacetate (0.50 mol, concentration 96%) and 61.80 g of 4-fluorobenzonitrile (0.50 mol, concentration 98%) were introduced into [500 ml of toluene and treated with 144.7 g of tin tetrachloride (0.55 mol, concentration 99%) at room temperature over the course of 16 min. After half an hour at room temperature, the thick suspension was heated to 80° C. After. 3 h, 175 ml of toluene were distilled off at normal pressure, and the mixture was cooled to room temperature and treated with 450 ml of saturated sodium carbonate and 300 ml of ethyl acetate. The organic phase was separated off and the aqueous phase (after dilution with 300 ml of water) was again extracted with 300 ml of ethyl acetate. After drying the combined organic phases over sodium sulphate, the solvent was removed in vacuo (40° C./25 mbar). 127.2 g of crude product were obtained in the form of a slightly yellowish solid, which was dissolved in 160 ml of n-hexane (slightly turbid solution). After hot filtration and subsequent cooling in an ice bath, 99.8 g of methyl 2-[1-amino-1-(4-fluorophenyl)-methylene]-4-methyl-3-oxopentanoate were obtained after filtration in the form of a pale yellow solid.

後処理

  1. waitAfter half an hour at room temperature
  2. distillation3 h, 175 ml of toluene were distilled off at normal pressure
  3. temperaturethe mixture was cooled to room temperature
  4. additiontreated with 450 ml of saturated sodium carbonate and 300 ml of ethyl acetate
  5. customThe organic phase was separated off
  6. extractionthe aqueous phase (after dilution with 300 ml of water) was again extracted with 300 ml of ethyl acetate
  7. dry with materialAfter drying the combined organic phases over sodium sulphate
  8. customthe solvent was removed in vacuo (40° C./25 mbar)
  9. custom127.2 g of crude product were obtained in the form of a slightly yellowish solid, which
  10. filtrationAfter hot filtration
  11. temperaturesubsequent cooling in an ice bath

出典と根拠

ORDレコード
ord-1f1b485b281146ec8dd6dd9e597da9cf
出典データセット
uspto-grants-2004_03
特許番号
US06710178B2

関連ノート

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