Iodoethane → Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)butanoate
Reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13](OCC)=O)[CH:9]=[CH:10][CH:11]=1.C([N-]C(C)C)(C)C.[Li+].CN(C)P(N(C)C)(N(C)C)=[O:34].ICC.[CH2:45]1[CH2:49][O:48][CH2:47][CH2:46]1>>[CH3:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:2]([CH3:1])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][CH2:46][C:47]([O:48][CH2:49][CH3:45])=[O:34])[CH:9]=[CH:10][CH:11]=1Participants
6
Conditions
- Temperature
- -78 °C
Procedure
To a stirred solution of Ethyl 2-(3-(2,6-dimethylbenzyloxy)phenyl)acetate (Step A, 4.79 g, 16.0 mmol) in dry THF (60 ml) was added drop wise a solution of lithium diisopropylamide (1.0 M in THF, 25 ml) at −78° C. under argon followed by addition of hexamethylphosphoramide (HMPA, 15 ml). After 15 minutes of stirring at −78° C., Iodoethane (12.53 g, 80.3 mmol) was added rapidly. The reaction mixture was warmed to room temperature for 16 hours. The crude mixture was quenched with sat. NH4Cl and extracted with ether (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (ethyl acetate:hexane, 1:4) to provide the title compound.
Workup
- temperatureThe reaction mixture was warmed to room temperature for 16 hours
- customThe crude mixture was quenched with sat. NH4Cl
- extractionextracted with ether (2×)
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- custompurified by flash chromatography on a silica gel column (ethyl acetate:hexane, 1:4)
Sources & evidence
- ORD record
- ord-3de7017e18fe4de7921724ee3a05bbf3
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115072B2
Reaction notes
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