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tert-Butyldimethylsilyl chloride → Silane, (1,1-dimethylethyl)dimethyl((4-(4-propyl-2,6,7-trioxabicyclo(2.2.2)oct-1-yl)phenyl)ethynyl)-

HRID 345379
Notes
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Reaction equation

HRID 345379 reaction equation
C([Li])CCC.[C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]23[O:21][CH2:20][C:17]([CH2:22][CH2:23][CH3:24])([CH2:18][O:19]2)[CH2:16][O:15]3)=[CH:10][CH:9]=1)#[CH:7].[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>O1CCCC1>[Si:25]([C:7]#[C:6][C:8]1[CH:9]=[CH:10][C:11]([C:14]23[O:15][CH2:16][C:17]([CH2:22][CH2:23][CH3:24])([CH2:18][O:19]2)[CH2:20][O:21]3)=[CH:12][CH:13]=1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 1152231-(4-Ethynylphenyl)-4-propyl-2,6,7-trioxabicyclo(2.2.2)octaneHCID 178418339Butyllithium

Product 1

HCID 3065686Silane, (1,1-dimethylethyl)dimethyl((4-(4-propyl-2,6,7-trioxabicyclo(2.2.2)oct-1-yl)phenyl)ethynyl)-

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Procedure

n-Butyllithium (0.79 ml of 1.6M solution, in hexane) was added to a stirred solution of 1-(4-ethynylphenyl)-4-n-propyl-2,6,7-trioxabicyclo[2,2,2]octane (0.25 g.) in dry tetrahydrofuran (15 ml) at 0°, under nitrogen. The reaction mixture was stirred at 0° for 10 minutes. t-Butyldimethylsilyl chloride (0.23 g.) was added and the mixture was stirred at room temperature for 6 hours. The reaction mixture was evaporated in vacuo. Water was added and the aqueous mixture was extracted with diethyl ether. The ethereal extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by chromatography on alumina (Alumina Woelm TSC), eluting with 2:3 dichloromethane:hexane saturated with ammonia. 1-[4-(2-t-Butyldimethylsilylethynyl)phenyl]-4-n-propyl-2,6,7-trioxabicyclo[2,2,2]octane was obtained as pale yellow crystals (0.32 g.).

Workup

  1. stirringthe mixture was stirred at room temperature for 6 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. additionWater was added
  4. extractionthe aqueous mixture was extracted with diethyl ether
  5. washThe ethereal extracts were washed with water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated in vacuo
  8. customThe residue was purified by chromatography on alumina (Alumina Woelm TSC)
  9. washeluting with 2:3 dichloromethane

Sources & evidence

ORD record
ord-aa8777e74d3742ba99972c4e7dc025dc
Source dataset
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05057508

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes