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

HRID 24718

반응식

HRID 24718 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 6344Dichloromethane용매2회

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-bf2c496b4c8e477298ee7b7da7604739
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855843B2

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