Sodium Carbonate → HCID 69230678, compound

HRID 661767Notes

Reaction equation

HRID 661767 reaction equation
[C:1]([C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][C:11]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:12][CH:13]=3)[CH2:8][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH2:27]([O:30][C:31]1[C:36]([C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:35][C:34]([CH3:41])=[CH:33][C:32]=1[Si:42](Cl)([CH2:46][CH2:47][CH3:48])[CH2:43][CH2:44][CH3:45])[CH:28]=[CH2:29].C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C(OCC)(=O)C.CCCCCC.C(N(CC)CC)C.C1(C)C=CC=CC=1>[CH2:27]([O:30][C:31]1[C:36]([C:37]([CH3:38])([CH3:39])[CH3:40])=[CH:35][C:34]([CH3:41])=[CH:33][C:32]=1[Si:42]([CH:8]1[C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:17]=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][C:11]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:12][CH:13]=2)([CH2:43][CH2:44][CH3:45])[CH2:46][CH2:47][CH3:48])[CH:28]=[CH2:29]

Participants

11

Reactant 5

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 40900822,7-Di-tert-butylfluoreneHCID 69229656HCID 69229656, compoundHCID 178418339Butyllithium

Product 1

HCID 69230678HCID 69230678, compoundYield 20.8%

Reagents, catalysts & solvents 5

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

There was dissolved 2.28 g (8.19 mmol) of 2,7-di-tert-butylfluorene in 37 mL of THF, and the obtained solution was cooled down to 0° C. To the solution, 5.19 mL of a 1.58 M-concentration hexane solution of n-butyllithium was added slowly, 5.19 mL of said hexane solution containing 8.20 mmol of n-butyllithium. Temperature of the resultant mixture was raised up to a room temperature, and the mixture was stirred for 1 hour at a room temperature. The mixture was cooled down to 0° C., and a solution of 2.89 g (8.17 mmol) of (2-allyloxy-3-tert-butyl-5-methyl phenyl)chlorodi-n-propylsilane in 9 mL of THF was added to the mixture. Temperature of the resultant mixture was raised up to a room temperature, and the mixture was stirred for 3 hours, thereby obtaining a reaction solution. A mixture of 50 mL of a 10% aqueous solution of sodium hydrogen carbonate and 50 mL of a 10% aqueous solution of sodium carbonate was added to the reaction solution at 0° C. To the obtained mixture, 58 mL of toluene was added, and the mixture was separated to the toluene solution and the aqueous solution. The toluene solution was dried over sodium sulfate, and the mixture was filtered. The obtained filtrate was concentrated under a reduced pressure. The concentrated filtrate was treated according to silica gel-column chromatography using, as a developing solvent, a 0.5% concentration-solution of triethylamine in a mixed solvent of 10 parts by volume of hexane and 1 part by volume of ethyl acetate, thereby obtaining 1.01 g (yield: 20.7%) of (2-allyloxy-3-tert-butyl-5-methylphenyl)(2,7-di-tert-butylfluoren-9-yl)di-n-propylsilane.

Workup

  1. concentrationTo the solution, 5.19 mL of a 1.58 M-concentration hexane solution of n-butyllithium
  2. additionwas added slowly
  3. temperatureThe mixture was cooled down to 0° C.
  4. stirringthe mixture was stirred for 3 hours
  5. customobtaining a reaction solution
  6. additionwas added to the reaction solution at 0° C
  7. customthe mixture was separated to the toluene solution
  8. dry with materialThe toluene solution was dried over sodium sulfate
  9. filtrationthe mixture was filtered
  10. concentrationThe obtained filtrate was concentrated under a reduced pressure
  11. additionThe concentrated filtrate was treated

Sources & evidence

ORD record
ord-3e5e4ffd7d9e4021836d13f38c67193c
Source dataset
uspto-grants-2011_12
Patent number
US08084559B2

Reaction notes

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