Ethyl isobutyrate → Ethyl 2,2-dimethyl-3-(naphthalene-2-yl)propanoate
Reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:11]([O:16][CH2:17][CH3:18])(=[O:15])[CH:12]([CH3:14])[CH3:13].Cl[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1>O1CCCC1>[CH3:13][C:12]([CH3:14])([CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1)[C:11]([O:16][CH2:17][CH3:18])=[O:15]Participants
Procedure
Lithium bis(trimethylsilyl)amide (1 M in tetrahydrofuran, 25.3 mL, 25.3 mmol) was added to a mixture of ethyl isobutyrate (2.67 g, 23.0 mmol) in tetrahydrofuran (25 mL) at −78° C. After stirring for 30 m, a solution of 2-(chloromethyl)naphthalene (400 mg, 2.30 mmol) in tetrahydrofuran (10 mL) was added to the reaction mixture dropwise. The mixture was stirred at −78° C. for another hour and then at room temperature overnight. The mixture was quenched by the addition of water and extracted with ethyl acetate. The combined organic fractions were washed with water, dried over sodium sulfate and concentrated under vacuum to give ethyl 2,2-dimethyl-3-(naphthalene-2-yl)propanoate (1.00 g) as a yellow oil, which was used without further purification.
Workup
- stirringThe mixture was stirred at −78° C. for another hour
- customat room temperature
- customovernight
- customThe mixture was quenched by the addition of water
- extractionextracted with ethyl acetate
- washThe combined organic fractions were washed with water
- dry with materialdried over sodium sulfate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-5f23ed9678864a6e9049328b601f6dd2
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09056852B2
Reaction notes
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