Triethylsilane → Diethyl acetamido(6-octyl-1,2,3,4-tetrahydronaphthalen-2-yl)propanedioate
Reaction equation
C([SiH](CC)CC)C.[CH2:8]([O:10][C:11](=[O:41])[C:12]([NH:37][C:38](=[O:40])[CH3:39])([CH:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:24]=2)[C:19]1=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:9]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH2:8]([O:10][C:11](=[O:41])[C:12]([NH:37][C:38](=[O:40])[CH3:39])([CH:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:24]=2)[CH2:19]1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:9]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of triethylsilane (1.3 ml, 8.2 mmol) in 5 ml of CH2Cl2 was added compound 5 (1 g, 2.1 mmol) in 5 ml of CH2Cl2. The reaction mixture was stirred at room temperature under Ar and TiCl4 (0.09 ml, 8.2 mmol) was added dropwise. The resulting solution was stirred for 12 hours, cooled to 0° C. and quenched by slow addition of 10 ml of saturated NaHCO3. The aqueous layer was extracted with CH2Cl2 (3×30 mL). The combined organic layers were washed with brine (2×30 mL) and dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography (Silica gel, 20% EtOAc in hexanes) to provide 630 mg of compound 6 (65%).
Workup
- additionwas added dropwise
- customquenched by slow addition of 10 ml of saturated NaHCO3
- extractionThe aqueous layer was extracted with CH2Cl2 (3×30 mL)
- washThe combined organic layers were washed with brine (2×30 mL)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under vacuum
- customThe residue was purified by column chromatography (Silica gel, 20% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-cea4b9a82b044f5a98846d4832e2fa0f
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173710B2
Reaction notes
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