Sodium Hydroxide → 4-formyl-[(2-propynyl)]-1H-pyrrole-2-carbonitrile

HRID 649028

反応式

HRID 649028 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]#[N:14])[C:6]#[CH:7].Cl[CH:16]([O:18]C(Cl)Cl)Cl.[OH-].[Na+]>C(Cl)Cl.O.[N+](C)([O-])=O>[CH:16]([C:11]1[CH:10]=[C:9]([C:13]#[N:14])[N:8]([CH2:5][C:6]#[CH:7])[CH:12]=1)=[O:18]

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 558102Bis(dichloromethyl) etherHCID 6451240Aluminum(III) ChlorideHCID 21278475HCID 21278475、化合物

生成物 1

HCID 136050134-formyl-[(2-propynyl)]-1H-pyrrole-2-carbonitrile収率 117%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回HCID 6375Nitromethane溶媒

反応条件

温度
-78 °C

実験手順

A mixture of 2.36 g of aluminium chloride in 6 ml of anhydrous methylene chloride was cooled to -78° C. and 1.3 g of the product of Step A in solution in 8 ml of methylene chloride and 0.5 ml of nitromethane were added. 1.49 g of dichloromethyl ether in solution in 15 ml of methylene chloride were added at -55° C. and the reaction mixture was kept for 1 hour at -60° C., then allowed to return to 20° C., at which temperature it was held for 18 hours. It was poured into water, stirred, and neutralized to pH 7 by addition of 33 ml of 2N sodium hydroxide. Extraction was with methylene chloride and the extracts were washed with a 1M potassium bicarbonate solution, dried and concentrated to dryness to obtain 1.5 g of 4-formyl-[(2-propynyl)]-1H-pyrrole-2-carbonitrile which was washed with dupentane and dried to obtain 1.1 g of the said product melting at 97° C.

後処理

  1. customto return to 20° C., at which temperature it
  2. waitwas held for 18 hours
  3. extractionExtraction
  4. washthe extracts were washed with a 1M potassium bicarbonate solution
  5. customdried
  6. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-7fb0004cb91b482aa238ed594670f3e0
出典データセット
uspto-grants-1988_04
特許番号
US04737513

関連ノート

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