Acetic Acid → Methyl 2-allyl-2-phenyl-4-pentenoate
Reaction equation
[C:1]1([CH2:7][C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:12](Br)[CH:13]=[CH2:14].[H-].[Na+].C(O)(=O)C.O1C[CH2:25][CH2:24][CH2:23]1>[I-].[Na+]>[CH2:12]([C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH2:25][CH:24]=[CH2:23])[C:8]([O:10][CH3:11])=[O:9])[CH:13]=[CH2:14]Participants
Conditions
- Temperature
- 25 °C
Procedure
A solution of methyl 2-phenylacetate (12.0 g, 80 mmol), allyl bromide (17.3 mL, 200 mmol) and sodium iodide (1 g) in tetrahydrofuran (160 mL) at 0° C. was treated portionwise with sodium hydride (7.36 g, 60% in oil, 184 mmol) over 10 minutes. The solution was allowed to warm to 25° C. and heated at reflux for 18 hours. The mixture was cooled to 0° C., treated with glacial acetic acid (2 mL) and concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic phase was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was filtered through a plug of 70-230 mesh silica gel eluting first with hexane and then with 10% ethyl acetate in hexane to give the title compound (17.89 g, 97%). 1H NMR (300 MHz, CDCl3): δ 7.29 (m, 5 H), 5.52 (m, 2 H), 5.06 (m, 4 H), 3.65 (s, 3 H), 2.78 (m, 4 H).
Workup
- temperatureheated
- temperatureat reflux for 18 hours
- temperatureThe mixture was cooled to 0° C.
- concentrationconcentrated in vacuo
- customThe residue was partitioned between ethyl acetate and water
- washThe organic phase was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- filtrationThe residue was filtered through a plug of 70-230 mesh silica gel eluting first with hexane
Sources & evidence
- ORD record
- ord-88b9b5a46af1446391244fc0a14f6e36
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07538105B2
Reaction notes
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