Water → 2,2,3,3-Tetramethyl-4,7,10-trioxa-3-silatridec-12-yne
Reaction equation
[Si:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][OH:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].O.[CH3:18][CH2:19][CH2:20]CCC>O1CCCC1.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:20][C:19]#[CH:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 5-(t-butyldimethylsilyloxy)-3-oxa-1-pentanol (2.16 g, 9.8 mmol) in dry tetrahydrofuran (20 ml) was added sodium hydride (432 mg, 60% in oil, 10.8 mmol) at room temperature. The mixture was stirred for 30 minutes, and propalgyl bromide (2.9 g, 19.6 mmol) was added thereto. The mixture was stirred at room temperature for 12 hours. After the reaction was completed, water was added thereto. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate, and filtered. The organic solvent was removed under reduced pressure to give a crude product. This crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=8:1) to give the title compound (950 mg, yield: 38%).
Workup
- stirringThe mixture was stirred at room temperature for 12 hours
- extractionThe resulting mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated saline solution
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- customThe organic solvent was removed under reduced pressure
- customto give a crude product
- customThis crude product thus obtained
Sources & evidence
- ORD record
- ord-486aeabdab91462684b384f10f955acb
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07074819B2
Reaction notes
Loading…