5-((1H-Pyrrol-2-YL)methyl)-1H-pyrrole-2-carbaldehyde → Dipyrromethane

HRID 20200

반응식

HRID 20200 반응식
[CH:1]1[CH:5]=[C:4]([CH2:6][C:7]2[NH:11][C:10](C=O)=[CH:9][CH:8]=2)[NH:3][CH:2]=1.C12C=C3N=C(C=C3)C=C3NC(C=C3)=CC3=NC(C=C3)=CC(N1)=CC=2>>[CH:9]1[CH:8]=[C:7]([CH2:6][C:4]2[NH:3][CH:2]=[CH:1][CH:5]=2)[NH:11][CH:10]=1

참가 물질

3

반응물 2

HCID 167326915-((1H-Pyrrol-2-YL)methyl)-1H-pyrrole-2-carbaldehydeHCID 13770524121H,22H-Porphine

생성물 1

HCID 140814Dipyrromethane수율 46%

실험 절차

1-Formyldipyrromethane 2 is the key precursor for the porphine synthesis described herein. Formylation of dipyrromethane via Vilsmeier or Grignard reagent mediated syntheses21 results in multiple byproducts, requiring tedious chromatographic separation for the purification of 1-formyldipyrromethane (2). The TLC and 1H NMR analyses of the crude reaction mixture obtained from Vilsmeier formylation of dipyrromethane showed the presence of three components: starting dipyrromethane (3), 1-formyldipyrromethane (2), 1,9-diformyldipyrromethane (4), and an unknown byproduct (tentatively assigned as a 2-formyldipyrromethane) in a ratio of 7:20:4:1. We were able to separate the desired 2 in 46% yield (without using a tin complexation strategy); however, the purification required lengthy column chromatography.

출처 및 근거

ORD 기록
ord-1ae614c9e1c44c79a850d45cef6482db
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745618B2

연결된 노트

불러오는 중…