3-Pyridineacrylic acid ethyl ester → 2-Propen-1-ol, 3-(3-pyridinyl)-

HRID 2081512Notes

Reaction equation

HRID 2081512 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][C:9](OCC)=[O:10])[CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][CH2:9][OH:10])[CH:2]=1

Participants

3

Reactant 2

HCID 5833373-Pyridineacrylic acid ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 35635042-Propen-1-ol, 3-(3-pyridinyl)-

Procedure

Ethyl 3-(3-pyridyl)acrylate was reduced using lithium aluminum hydride to give 3-(3-pyridyl)-2-propen-1-ol. In 30 ml of acetone 710 mg of 3-(3-pyridyl)-2-propen-1-ol and 980 mg of methyl p-toluenesulfonate were heated under reflux for 22 hours. The reaction mixture was subjected by decantation to remove the solvent and then washed with acetone and ether. The residue was dried under reduced pressure to give 1.3 g of the desired compound as an orange-colored oil.

Sources & evidence

ORD record
ord-f9a0bdc04f6a44d39020f2a47ea7f943
Source dataset
uspto-grants-1993_02
Patent number
US05183811

Reaction notes

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