MeOH tetrahydrofuran → HCID 89853927, compound

HRID 1499332Notes

Reaction equation

HRID 1499332 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([Si:13]([C:28]2[CH:33]=[CH:32][C:31]([C:34]#[C:35][Si](C)(C)C)=[CH:30][CH:29]=2)([CH3:27])[O:14][Si:15]([CH3:26])([CH3:25])[O:16][Si:17]([CH3:24])([CH3:23])[O:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[CH:9][CH:8]=1)(C)C.CO.C1COCC1>CO.C1COCC1.N.O>[C:6]([C:7]1[CH:8]=[CH:9][C:10]([Si:13]([C:28]2[CH:29]=[CH:30][C:31]([C:34]#[CH:35])=[CH:32][CH:33]=2)([CH3:27])[O:14][Si:15]([CH3:26])([CH3:25])[O:16][Si:17]([CH3:23])([CH3:24])[O:18][Si:19]([CH3:20])([CH3:21])[CH3:22])=[CH:11][CH:12]=1)#[CH:5]

Participants

4

Reactant 2

HCID 21899815MeOH tetrahydrofuranHCID 89854450HCID 89854450, compound

Product 1

HCID 89853927HCID 89853927, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 178420687HCID 178420687, compoundSolvent

Procedure

Tetramethylsilane (TMS) was deprotonated through a reaction with an ammonia solution to produce the target monomer bis-(4-ethynylphenyl)-octamethyltetrasiloxane. Specifically, 1.00 g bis-(4-trimethylsilylethynylphenyl)-octamethyltetrasiloxane in MeOH/THF/NH3—H2O mixture (generally 1:1:1, but sometimes it is necessary to adjust MeOH/THF ratio to obtain transparent reaction mixture) was placed in a round-bottomed flask equipped with a magnetic stirring bar. The flask was placed in an ice-water bath and stirred for 24 h (monitored by TLC). Then, the reaction was stopped, and the mixture was extracted via DCM and water. After removing the solvent of the organic layer, Bis-(4-ethynylphenyl)-octamethyltetrasiloxane was obtained in a 61% yield as a light yellow liquid by running silica column with hexane/DCM (10:1) as eluent.

Workup

  1. customto obtain transparent reaction mixture)
  2. customwas placed in a round-bottomed flask
  3. customequipped with a magnetic stirring bar
  4. customThe flask was placed in an ice-water bath
  5. extractionthe mixture was extracted via DCM and water
  6. customAfter removing the solvent of the organic layer

Sources & evidence

ORD record
ord-fa8eede63f454c8e8debf6cf0b314a19
Source dataset
uspto-grants-2015_12
Patent number
US09200121B2

Reaction notes

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