4-Vinylbenzoic acid → Ethyl 4-vinylbenzoate
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
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. PMR (CDCl3): δ 1.39 (3 H, t, J=7.2 Hz), 4.37 (2 H, q, J=7.2 Hz), 5.38 (1 H, d, J=10.8 Hz), 5.86 (1 H, d, J=17.6 Hz), 6.75 (1 H, dd, J=10.8, 17.6 Hz), 7.46 (2 H, d, J=8.4 Hz), 8.00 (2 H, d, J=8.4 Hz).
Sources & evidence
- ORD record
- ord-5b746e6fb8ef4b50b3c134c5817cd6b9
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06187950B1
Reaction notes
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