Chlorotrimethylsilane → ((Dihydrofuran-2(3H)-ylidene)(methoxy)-methoxy)trimethylsilane
Reaction equation
[Li+].CC([N-]C(C)C)C.[O:9]1[CH2:13][CH2:12][CH2:11][CH:10]1[C:14]([O:16][CH3:17])=[O:15].[Si:18](Cl)([CH3:21])([CH3:20])[CH3:19]>C1COCC1>[O:9]1[CH2:13][CH2:12][CH2:11][C:10]1=[C:14]([O:16][CH3:17])[O:15][Si:18]([CH3:21])([CH3:20])[CH3:19]Participants
5
Conditions
- Temperature
- -78 °C
Procedure
To a suspension of LDA (2.6 g, 24.3 mmol) in THF (30 mL) at −78° C. was slowly added methyl tetrahydrofuran-2-carboxylate (3.0 g, 23.0 mmol). The resulting mixture was stirred at −78° C. for 20 minutes, and TMS chloride (2.6 g, 24.3 mmol) was slowly added. The reaction was stirred for 1 hour at −78° C. and then warmed to room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, avoiding contact with water. Hexanes (20 mL) was then added, and the mixture was passed through a short plug of celite, eluting with hexanes (10 mL). The solution was then concentrated, affording the crude product in good purity.
Workup
- stirringThe reaction was stirred for 1 hour at −78° C.
- temperaturewarmed to room temperature for 2 hours
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionHexanes (20 mL) was then added
- washeluting with hexanes (10 mL)
- concentrationThe solution was then concentrated
Sources & evidence
- ORD record
- ord-c7776747b56d4a5098e3e1e9b3059cff
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07928139B2
Reaction notes
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