4-Vinylbenzoic acid → Ethyl 4-vinylbenzoate

HRID 431695

Reaction equation

HRID 431695 reaction equation
F[C:2]1[CH:16]=[C:15](I)[CH:14]=[CH:13][C:3]=1[C:4]([O:6][CH2:7][CH2:8][Si](C)(C)C)=[O:5].[CH:18](C1C=CC(C(O)=O)=CC=1)=[CH2:19]>>[CH:18]([C:15]1[CH:14]=[CH:13][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:2][CH:16]=1)=[CH2:19]

Participants

3

Reactant 2

HCID 140984-Vinylbenzoic acidHCID 54147505Trimethylsilanylethyl 2-fluoro-4-iodobenzoate2×

Product 1

HCID 10866858Ethyl 4-vinylbenzoate

Procedure

Employing the same general procedure as for the preparation of trimethylsilanylethyl 2-fluoro-4-iodobenzoate (Compound D), 323 mg (2.2 mmol) of 4-vinylbenzoic acid was converted into the title compound using 462 mg (2.4 mmol) of 1-(3-dimethylaminopropyl-3-ethyl carbodiimide hydrochloride), 264 mg (2.2 mmol) of 4-dimethylaminopyridine, 0.32 ml (250 mg, 5.45 mmol) of ethanol and 16 mL of dichloromethane. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) gave the title compound as a clear, colorless oil.

Sources & evidence

ORD record
ord-36d24688f328439198ba53fc5889ed9a
Source dataset
uspto-grants-2003_12
Patent number
US06660755B2

Linked notes

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