4-Bromothiophene-3-carboxaldehyde → HCID 22503031, 화합물

HRID 1814492노트

반응식

HRID 1814492 반응식
[CH:1]([C:3]1[C:7](Br)=[CH:6][S:5][CH:4]=1)=[O:2].[CH3:9][O:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]#[CH:20])=[CH:15][CH:14]=1>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(N(CC)CC)C>[CH3:9][O:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:7]2[C:3]([CH:1]=[O:2])=[CH:4][S:5][CH:6]=2)=[CH:15][CH:14]=1

참가 물질

6

반응물 2

HCID 27642074-Bromothiophene-3-carboxaldehydeHCID 225029951-Ethynyl-4-(methoxymethoxy)benzene

생성물 1

HCID 22503031HCID 22503031, 화합물수율 66.9%

시약·촉매·용매 3

HCID 8471Triethylamine촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

3-Formyl-4-bromothiophene (14.7 g) was dissolved in DMF (100 ml), followed by the addition of triethylamine (100 ml) CuI (0.25 g), Pd(PPh3)2Cl2 (0.5 g) and 4-methoxymethoxy-1-ethynylbenzene (11.4 g), and the mixture was reacted at 70° C. overnight. The reaction solution was filtered through Celite, poured into 1N hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with an aqueous solution of saturated sodium bicarbonate and brine, dried and evaporated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system), to give 3-{[4-(methoxymethoxy)phenyl]ethynyl}-4-formylthiophene as a colorless oil (12.8 g, yield; 47%).

후처리

  1. customthe mixture was reacted at 70° C. overnight
  2. filtrationThe reaction solution was filtered through Celite
  3. additionpoured into 1N hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous solution of saturated sodium bicarbonate and brine
  6. customdried
  7. customevaporated
  8. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

출처 및 근거

ORD 기록
ord-0246105bfa19470789925f21a1f1695b
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875761B2

반응 노트

불러오는 중…