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

HRID 1756

Reaction equation

HRID 1756 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 (1.1 ml, 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-7962bc1b7397448eac87976efef7cca2
Source dataset
uspto-grants-1998_03
Patent number
US05726315

Linked notes

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