Potassium Iodide → methyl (4E)-2-acetyl-5-phenyl-4-pentenoate

HRID 1368294

Reaction equation

[CH3:1][O:2][C:3](=[O:8])/[CH:4]=[C:5](/[O-:7])\[CH3:6].[Na+].[I-].[K+].Br[CH2:13]/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:5]([CH:4]([CH2:13]/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]([O:2][CH3:1])=[O:8])(=[O:7])[CH3:6]

Participants

Reactant 3

HCID 4875Potassium Iodide

HCID 5357478Cinnamyl bromide

HCID 23681258sodium (2E)-4-methoxy4-oxo-2-buten-2-olate

Product 1

HCID 11020753methyl (4E)-2-acetyl-5-phenyl-4-pentenoate

Procedure

Analogously to Example 28A, 10 g (72.4 mmol) of sodium (2E)-4-methoxy-4-oxo-2-buten-2-olate and 0.40 g (2.41 mmol) of potassium iodide are reacted with 14.3 g (72.4 mmol) of [(1E)-3-bromo-1-propenyl]benzene to give methyl (4E)-2-acetyl-5-phenyl-4-pentenoate.

Sources & evidence

ORD record: ord-bbee9c6118c04db7923aaaa574d1a179
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573263B2

Linked notes

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