Water → 2-[1,1,1,3,3,3-Hexamethyl-2-(trimethylsilyl)trisilan-2-yl]ethan-1-ol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][CH2:11][CH2:12][Si:13]([Si:22]([CH3:25])([CH3:24])[CH3:23])([Si:18]([CH3:21])([CH3:20])[CH3:19])[Si:14]([CH3:17])([CH3:16])[CH3:15])(=O)C.O.[OH-].[Na+]>O1CCCC1>[CH3:17][Si:14]([Si:13]([Si:22]([CH3:25])([CH3:24])[CH3:23])([Si:18]([CH3:21])([CH3:20])[CH3:19])[CH2:12][CH2:11][OH:10])([CH3:15])[CH3:16]Participants
Procedure
A solution of 3.8 g lithium aluminum hydride (LiAlH4) in 100 ml tetrahydrofuran was stirred at 5° C. in an argon atmosphere. To the solution, 33.5 g of 2-[tris(trimethylsilyl)silyl]ethyl acetate was added dropwise. After one hour of stirring at 5° C., with ice cooling, 3.8 ml of water, 3.8 ml of 15% aqueous sodium hydroxide, and 11.4 ml of water were successively added to the solution in the described order. The mixture was stirred for one hour at room temperature. The resulting precipitate was filtered off, and the tetrahydrofuran solution was dried and concentrated, obtaining 24.8 g of 2-[tris(trimethylsilyl)silyl]ethanol. This crude product was dissolved in a solvent and analyzed by gas chromatography, finding that it contained 98.2% of 2-[tris(trimethylsilyl)silyl]ethanol. This was esterified with methacryloyl chloride in the presence of triethylamine as the base as in Comparative Example 1. Subsequent extraction and vacuum distillation for purification gave 29.5 g of the end compound, 2-[tris(trimethylsilyl)silyl]ethyl methacrylate. The yield throughout the two steps was 82%.
Workup
- additionwere successively added to the solution in the described order
- filtrationThe resulting precipitate was filtered off
- dry with materialthe tetrahydrofuran solution was dried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a5cf0591a103440b81d13cf7ac110119
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06291696B1
Reaction notes
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