Hexane → Ethyl 5-phenylpent-2-enoate
Reaction equation
[CH2:1]1CCC(N=C=NC2CCCCC2)C[CH2:2]1.[C:16]1([CH2:22][CH2:23][CH:24]=[CH:25][C:26]([OH:28])=[O:27])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCCCCC>CN(C1C=CN=CC=1)C.CCO.C1COCC1>[CH2:1]([O:27][C:26](=[O:28])[CH:25]=[CH:24][CH2:23][CH2:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:2]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
The reagents DCC (33 mM) and DMAP (30 mM) were added to a solution of 5-phenylpent-2-enoic acid (5.3 g, 30 mM) in EtOH (50 mL) and THF (20 mL), which was cooled to 0° C. The resulting mixture was stirred for 30 min at 0° C., then allowed to react for 15 h at room temperature. The suspension was filtered, and the filtrate was concentrated. The residue was dissolved in EtOAc and washed with 1 M HCl (3×30 mL), H2O (10 mL), saturated NaHCO3 (3×30 mL), H2O (10 mL), saturated NaCl (20 mL), dried over MgSO4, and concentrated. Chromatography on a silica gel column using 1:2 EtOAc:hexane as the eluent afforded 5-phenyl-pent-2-enoic acid ethyl ester (3.75 g, yield=61%).
Workup
- customto react for 15 h at room temperature
- filtrationThe suspension was filtered
- concentrationthe filtrate was concentrated
- dissolutionThe residue was dissolved in EtOAc
- washwashed with 1 M HCl (3×30 mL), H2O (10 mL), saturated NaHCO3 (3×30 mL), H2O (10 mL), saturated NaCl (20 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8beb8a76caed4413b209fbbfcb6cd652
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07056947B2
Reaction notes
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