Water → HCID 20209698, compound
Reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].Br[C:7]1[CH:11]=[CH:10][O:9][CH:8]=1.Cl[Si:13]([CH3:24])([CH3:23])[O:14][Si:15]([CH3:22])([CH3:21])[O:16][Si:17]([CH3:20])([CH3:19])Cl.[OH2:25]>O1CCCC1>[O:25]1[CH:4]=[CH:3][C:2]([Si:13]([CH3:24])([CH3:23])[O:14][Si:15]([CH3:22])([CH3:21])[O:16][Si:17]([CH3:20])([CH3:19])[C:7]2[CH:11]=[CH:10][O:9][CH:8]=2)=[CH:1]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Twenty-two (22) ml of n-butyllithium (1.55M in hexane) and 5 ml dry tetrahydrofuran (THF) were added under nitrogen to a 250 ml round-bottomed flask equipped with a magnetic stirrer. The solution was cooled to -78 degrees C. Five (5) grams of 3-Bromofuran in 10 ml dry THF were then added dropwise under nitrogen, with constant stirring. The solution was stirred for 1 hour upon which a slurry formed. 4.718 g of 1,5-dichlorohexamethyl trisiloxane in 10 ml dry THF were then added dropwise under nitrogen. The solution was then stirred for 4 hours, during which time it was allowed to come to room temperature. The solution was poured into 30 ml of water containing 3 ml conc. HCl. The organic layer was removed, and the aqueous layer extracted with 3×20 ml portions of ether. The organic layers were combined, dried using anhydrous Na2SO4, and filtered. The solvents were removed in vacuo, to give 4.2 g of an orange liquid.
Workup
- customequipped with a magnetic stirrer
- customformed
- stirringThe solution was then stirred for 4 hours, during which time it
- customto come to room temperature
- customThe organic layer was removed
- extractionthe aqueous layer extracted with 3×20 ml portions of ether
- customdried
- filtrationfiltered
- customThe solvents were removed in vacuo
Sources & evidence
- ORD record
- ord-535591a6b20340cdae1f6bd8fe83d79a
- Source dataset
- uspto-grants-1987_04
- Patent number
- US04656235
Reaction notes
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