Water → 5-[3-(1-imidazolyl)propyl]-2-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]pyridine

HRID 322445노트

반응식

HRID 322445 반응식
[H-].[Na+].[C:3]1(/[CH:9]=[CH:10]/[C:11]2[O:12][CH:13]=[C:14]([CH2:16][OH:17])[N:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)=[CH:21][N:20]=1.O>CN(C)C=O>[N:28]1([CH2:27][CH2:26][CH2:25][C:22]2[CH:23]=[CH:24][C:19]([O:17][CH2:16][C:14]3[N:15]=[C:11](/[CH:10]=[CH:9]/[C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)[O:12][CH:13]=3)=[N:20][CH:21]=2)[CH:32]=[CH:31][N:30]=[CH:29]1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 13657827(E)-(2-Styryloxazol-4-yl)methanolHCID 220095902-Chloro-5-[3-(1-imidazolyl)propyl]pyridine

생성물 1

HCID 220097425-[3-(1-imidazolyl)propyl]-2-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]pyridine수율 47%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
90 °C

실험 절차

Sodium hydride (oily, 60%, 660 mg) was added to a solution of 2-[(E)-2-phenylethenyl]-4-oxazolylmethanol (3.02 g) in N,N-dimethylformamide (30 ml) and stirred at 90° C. for 30 minutes, to which was added a solution of 2-chloro-5-[3-(1-imidazolyl)propyl]pyridine (1.10 g) in N,N-dimethylformamide (10 ml). The resultant was stirred at 90° C. for 14 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium bicarbonate and brine, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane-methanol (10:1:0.5, v/v), crystals of 5-[3-(1-imidazolyl)propyl]-2-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]pyridine (900 mg, 47%) was obtained. Recrystallization ethyl acetate-hexane gave pale brown prisms, mp 120-121° C.

후처리

  1. stirringThe resultant was stirred at 90° C. for 14 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. washFrom the fraction eluted with ethyl acetate-hexane-methanol (10:1:0.5

출처 및 근거

ORD 기록
ord-ab516d3c6d474f2da2f6620fcea14b6e
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211215B1

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