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

HRID 1089152Notes

Reaction equation

HRID 1089152 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]

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 8028TetrahydrofuranSolvent

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-7f0bc1ec45024373889bd2ee8ef6292c
Source dataset
uspto-grants-1990_10
Patent number
US04965257

Reaction notes

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