Oxalyl chloride → 2-Chloro-4-(2-formyl-1-pyrrolyl)benzoic acid methyl ester

HRID 24718

反応式

HRID 24718 の反応式
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[CH3:7][O:8][C:9](=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([N:16]2C=[CH:19][CH:18]=[CH:17]2)=[CH:12][C:11]=1[Cl:21]>C(Cl)Cl.CN(C=O)C>[CH3:7][O:8][C:9](=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:17]=[CH:18][CH:19]=[C:2]2[CH:1]=[O:5])=[CH:12][C:11]=1[Cl:21]

参加物

5

反応物 2

HCID 65578Oxalyl chlorideHCID 47637352-Chloro-4-(1-pyrrolyl)benzoic acid methyl ester

生成物 1

HCID 538123242-Chloro-4-(2-formyl-1-pyrrolyl)benzoic acid methyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of DMF (0.1 mL) in CH2Cl2 (2 mL) was added dropwise with stirring to a solution of oxalyl chloride (0.2 mL) in CH2Cl2 (16 mL) at −30° C. under N2. The mixture was stirred for 15 min and a solution of 2-chloro-4-(1-pyrrolyl)benzoic acid methyl ester (0.5 g) in DMF (4 mL) was added. The mixture was stirred at that temperature for 3 h and allowed to warm to room temperature. The mixture was stirred overnight and evaporated. The residue was partitioned between EtOAc and 0.2 M NaOAc. The EtOAc layer was separated and the aqueous solution was extracted with EtOAc. The combined EtOAc layer was washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (silica gel; eluent: hexane/EtOAc 3/1) to yield 2-chloro-4-(2-formyl-1-pyrrolyl)benzoic acid methyl ester (0.41 g). ESMS: 264 (MH+).

後処理

  1. stirringThe mixture was stirred at that temperature for 3 h
  2. stirringThe mixture was stirred overnight
  3. customevaporated
  4. customThe residue was partitioned between EtOAc and 0.2 M NaOAc
  5. customThe EtOAc layer was separated
  6. extractionthe aqueous solution was extracted with EtOAc
  7. washThe combined EtOAc layer was washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by column chromatography (silica gel; eluent: hexane/EtOAc 3/1)

出典と根拠

ORDレコード
ord-bf2c496b4c8e477298ee7b7da7604739
出典データセット
uspto-grants-2005_02
特許番号
US06855843B2

関連ノート

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