4-Fluorobenzoyl chloride → HCID 18424154、化合物

HRID 1282368ノート

反応式

HRID 1282368 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:15][N:16]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]1[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>ClCCCl>[CH3:15][N:16]1[C:20]([C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)=[C:19]([CH3:21])[CH:18]=[C:17]1[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

参加物

5

反応物 3

HCID 678794-Fluorobenzoyl chlorideHCID 118467Ethyl 1,4-dimethyl-1H-pyrrole-2-acetateHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 18424154HCID 18424154、化合物収率 25%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒2 回

実験手順

A solution of 3.95 g. (0.025 mole) of p-fluorobenzoyl chloride and 3.32 g. (0.025 mole) of aluminum chloride in 20 ml. of 1,2-dichloroethane is added dropwise to a solution of 4.52 g. (0.025 mole) of ethyl 1,4-dimethylpyrrole-2-acetate in 20 ml. of 1,2-dichloroethane at room temperature. The reaction mixture is stirred for 2 hours, and then cooled and poured into ice-dilute HCl. The organic phase is separated and washed successively with N,N-dimethyl-1,3-propanediamine, dilute hydrochloric acid and a saturated solution of sodium chloride; dried over anhydrous magnesium sulfate; and the solvent evaporated. The residue is triturated with hot hexane and crystals form upon cooling. There is obtained about 1.9 g. (25% yield) of ethyl 1,4-dimethyl-5-(p-fluorobenzoyl)-pyrrole-2-acetate as a white solid, m.p. 84-86° C. Upon recrystallization from methanol, the m.p. is 87-89° C.

後処理

  1. customat room temperature
  2. temperaturecooled
  3. additionpoured into ice-dilute HCl
  4. customThe organic phase is separated
  5. washwashed successively with N,N-dimethyl-1,3-propanediamine, dilute hydrochloric acid
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customand the solvent evaporated
  8. customThe residue is triturated with hot hexane and crystals
  9. customform
  10. temperatureupon cooling
  11. customThere is obtained about 1.9 g

出典と根拠

ORDレコード
ord-4f70cac99b42464f81354ef206c8a21f
出典データセット
uspto-grants-2002_09
特許番号
US06455703B2

反応ノート

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