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

HRID 1756
Notes
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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
ParticipantsConditionsProcedureSources & evidenceReaction notes

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 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05726315

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes