Sodium Carbonate → HCID 178458912, compound

HRID 661765Notes

Reaction equation

HRID 661765 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[SiH:42]([CH2:44][CH2:45]Cl)[CH3:43])[CH:28]=[CH2:29].C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C1(C)C=CC=CC=1.CCCCCC>[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[SiH:42]([CH2:44][CH2:45][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)[CH3:43])[CH:28]=[CH2:29]

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 40900822,7-Di-tert-butylfluoreneHCID 131729330HCID 131729330, compoundHCID 178418339Butyllithium

Product 1

HCID 178458912HCID 178458912, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

There was dissolved 2.00 g (7.18 mmol) of 2,7-di-tert-butylfluorene in 45 mL of THF, and the obtained solution was cooled down to −78° C. To the solution, 4.49 mL of a 1.60 M-concentration hexane solution of n-butyllithium was added slowly, 4.49 mL of said hexane solution containing 7.18 mmol of n-butyllithium. Temperature of the resultant mixture was raised up to a room temperature, and the mixture was stirred for 3 hours at a room temperature. The mixture was cooled down to −78° C., and a solution of 2.23 g (7.18 mmol) of (2-allyloxy-3-tert-butyl-5-methyl phenyl)chloroethylmethylsilane in 9 mL of toluene 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 20 mL of a 10% aqueous solution of sodium hydrogen carbonate and 20 mL of a 10% aqueous solution of sodium carbonate was added to the reaction solution at 0° C. To the obtained mixture, 23 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, thereby obtaining quantitatively (2-allyloxy-3-tert-butyl-5-methylphenyl)(2,7-di-tert-butyl fluoren-9-yl)ethylmethylsilane.

Workup

  1. concentrationTo the solution, 4.49 mL of a 1.60 M-concentration hexane solution of n-butyllithium
  2. additionwas added slowly
  3. temperatureThe mixture was cooled down to −78° 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

Sources & evidence

ORD record
ord-5df540ee15214375a51cd725a15262cc
Source dataset
uspto-grants-2011_12
Patent number
US08084559B2

Reaction notes

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