Sodium Carbonate → HCID 67388168, compound

HRID 1257562Notes

Reaction equation

HRID 1257562 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[CH:5][CH:6]=1.C([Li])CCC.B(OC(C)C)(OC(C)C)OC(C)C.C(=O)([O-])[O-].[Na+].[Na+].Br[C:32]1[CH2:33][C:34]2[C:39]([CH:40]=1)=[C:38]([C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=1)[C:37]([CH3:49])=[CH:36][CH:35]=2>COCCOC.CCCCCC.C1(P([Pd](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:1][C:2]1[O:3][C:4]([C:32]2[CH2:33][C:34]3[C:39]([CH:40]=2)=[C:38]([C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=2)[C:37]([CH3:49])=[CH:36][CH:35]=3)=[CH:5][CH:6]=1

Participants

10

Reactant 5

HCID 10340Sodium CarbonateHCID 107972-MethylfuranHCID 21531Triisopropyl borateHCID 67328409HCID 67328409, compoundHCID 178418339Butyllithium

Product 1

HCID 67388168HCID 67388168, compound

Reagents, catalysts & solvents 4

HCID 178420554HCID 178420554, compoundCatalystHCID 962WaterSolventHCID 8058HexaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
-30 °C

Procedure

Solution of 2-methylfuran (1.9 g, 23 mmol) in absolute DME was cooled at −70° C., and solution of n-butyllithium in n-hexane (1.66 M, 14 mL) was dropped. Reaction solution was stirred for 3 hours at low temperature of about −30° C. as it was, subsequently, triisopropyl borate (5.9 mL, 25.5 mmol) was added, and reaction solution was stirred at room temperature day and night. After stirring, distilled water (5 mL) was added to hydrolyze, and aqueous solution (20 mL) of sodium carbonate (4.8 g, 45 mmol), crude product of 2-bromo-4-(4-methoxyphenyl)-5-methylindene synthesized in the above, further, tetrakis(triphenylphosphino)palladium (0.6 g) were added, and heated for 2.5 hours under reflux. Water was added to the reaction solution to separate organic layer, organic layer was filtered through Celite, and washed with saturated solution of sodium chloride, and dried over magnesium sulfate, and solvent was distilled off under reduced pressure.

Workup

  1. customReaction solution
  2. customreaction solution
  3. stirringwas stirred at room temperature day and night
  4. stirringAfter stirring
  5. distillationdistilled water (5 mL)
  6. additionwas added
  7. additionwere added
  8. temperatureheated for 2.5 hours
  9. temperatureunder reflux
  10. customto separate organic layer, organic layer
  11. filtrationwas filtered through Celite
  12. washwashed with saturated solution of sodium chloride
  13. dry with materialdried over magnesium sulfate, and solvent
  14. distillationwas distilled off under reduced pressure

Sources & evidence

ORD record
ord-55d678c888304a0dba784ae997c2c778
Source dataset
uspto-grants-2013_06
Patent number
US08461365B2

Reaction notes

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