Ethyl Acrylate → Ethyl (3-benzyloxy-6-hydroxymethylpyridin-2-yl)propenoate

HRID 264789

Reaction equation

HRID 264789 reaction equation
[CH2:1]([O:8][C:9]1[C:10](I)=[N:11][C:12]([CH2:15][OH:16])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].[C:23]([O:27][CH2:28][CH3:29])(=[O:26])[CH:24]=[CH2:25]>CN(C=O)C.O>[CH2:1]([O:8][C:9]1[C:10]([C:24](=[CH2:25])[C:23]([O:27][CH2:28][CH3:29])=[O:26])=[N:11][C:12]([CH2:15][OH:16])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8821Ethyl AcrylateHCID 517044Potassium AcetateHCID 196927123-Benzyloxy-6-hydroxymethyl-2-iodopyridine

Product 1

HCID 86751041Ethyl (3-benzyloxy-6-hydroxymethylpyridin-2-yl)propenoateYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-benzyloxy-6-hydroxymethyl-2-iodopyridine (1.20 g, 3.50 mmol) in DMF (6.4 ml) and water (0.32 ml) were added potassium acetate (0.83 g, 8.5 mmol) palladium acetate (32 mg, 0.14 mmol) and ethyl acrylate (1.1ml, 1.01 g, 10 mmol). The mixture was placed under nitrogen and stirred and heated at 120° C. for 1.25 h. By hplc the solution yield was 62%.

Sources & evidence

ORD record
ord-3b9686b7cdd04c39bcff3ecc3658d90a
Source dataset
uspto-grants-1997_07
Patent number
US05646286

Linked notes

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