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

HRID 322445Notes

Reaction equation

HRID 322445 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ab516d3c6d474f2da2f6620fcea14b6e
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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