Methanol → Methyl 4-[3-(3-benzyloxy-2-pyridyl)prop-2-enyl]benzoate

HRID 2395076Notes

Reaction equation

HRID 2395076 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH:15]=[CH:16][CH2:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:31]O>>[CH2:1]([O:8][C:9]1[C:10]([CH:15]=[CH:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:22]([O:24][CH3:31])=[O:23])=[CH:25][CH:26]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 544494594-[3-(3-Benzyloxy-2-pyridyl)prop-2-enyl)benzoic acid

Product 1

HCID 54508749Methyl 4-[3-(3-benzyloxy-2-pyridyl)prop-2-enyl]benzoateYield 49%

Conditions

Temperature
0 °C

Procedure

4-[3-(3-Benzyloxy-2-pyridyl)prop-2-enyl)benzoic acid (0.1 g, 0.29 mmol) was dissolved in methanol (5 ml) and cooled to 0° C. To the solution was added thionyl chloride (0.086 g, 0.73 mmol). The reaction was allowed to warm to ambient temperature and stirred at ambient temperature for 18 hours. The reaction mixture was then evaporated, the residue partitioned between ethyl acetate and water and the organic phase dried (MgSO4) and evaporated. The residue was purified by chromatography (SiO2 EtOAc/CH2Cl2) to give methyl 4-[3-(3-benzyloxy-2-pyridyl)prop-2-enyl]benzoate as an oil (0.05 g, 49%).

Workup

  1. temperatureto warm to ambient temperature
  2. customThe reaction mixture was then evaporated
  3. customthe residue partitioned between ethyl acetate and water
  4. dry with materialthe organic phase dried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by chromatography (SiO2 EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-0999835e5f0d44ac90f78734e89367ce
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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