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Water → HCID 20209698, compound

HRID 542245
Notes
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Reaction equation

HRID 542245 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]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 771311,5-Dichloro-1,1,3,3,5,5-hexamethyltrisiloxaneHCID 891643-BromofuranHCID 178418339Butyllithium

Product 1

HCID 20209698HCID 20209698, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent
3×

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

  1. customequipped with a magnetic stirrer
  2. customformed
  3. stirringThe solution was then stirred for 4 hours, during which time it
  4. customto come to room temperature
  5. customThe organic layer was removed
  6. extractionthe aqueous layer extracted with 3×20 ml portions of ether
  7. customdried
  8. filtrationfiltered
  9. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-535591a6b20340cdae1f6bd8fe83d79a
Source dataset
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04656235

Reaction notes

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