Water → HCID 21965165, compound

HRID 2358915Notes

Reaction equation

HRID 2358915 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH:6]1[C:14]2[C:13]3[CH:15]=CC=[CH:18][C:12]=3[O:11][C:10]=2[CH:9]=[CH:8][C:7]=1C=O.O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCCCCC.C1COCC1>[CH:3]([C:2]1[CH:1]=[CH:18][C:12]2[O:11][C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:14]=3[C:13]=2[CH:15]=1)=[CH2:4]

Participants

7

Reactant 3

HCID 962WaterHCID 220843Dibenzo(b,d)furan-2-carboxaldehydeHCID 178418339Butyllithium

Product 1

HCID 21965165HCID 21965165, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

22.7 g (63.7 mmol) of Methyl triphenylphosphonium bromide and 200 ml of dry THF are placed in a dried 500 ml three necked round bottomed flask, equipped with a magnetic stirrer and the reaction mixture is cooled to 0° C. internal temperature with a NaCl/ice bath. 41.8 ml (66.9 mmol) of 1.6 M Butyl lithium solution in Hexane are added within 30 minutes while keeping the internal temperature below 3° C. The reaction mixture is stirred at the same temperature for 45 minutes, then 47.2 mmol of Dibenzofuran-2-carboxaldehyde dissolved in 100 ml of dry THF are added within 30 minutes. After two hours the reaction mixture is warmed to room temperature, added to 500 ml of water and extracted three times with 500 ml of Ethylacetate. The combined organic phases are washed once with 500 ml of a 1:1 mixture of buffer pH=1 and brine, once with 30 ml of brine, dried over Magnesiumsulfate, filtered and evaporated. The crude product is dissolved in Dichloromethane, 100 g of silica are added and the solvent is evaporated. The resulting powder is added on top of 300 g of silica in a sintered glass funnel and the product eluted with Hexane/Ethylacetate=8:1. The product is crystallized from 2-Propanol. 2-Vinyl-dibenzofuran is isolated in 95% yield.

Workup

  1. customequipped with a magnetic stirrer
  2. customthe internal temperature below 3° C
  3. additionare added within 30 minutes
  4. temperatureAfter two hours the reaction mixture is warmed to room temperature
  5. extractionextracted three times with 500 ml of Ethylacetate
  6. washThe combined organic phases are washed once with 500 ml of a 1:1 mixture of buffer pH=1 and brine, once with 30 ml of brine
  7. dry with materialdried over Magnesiumsulfate
  8. filtrationfiltered
  9. customevaporated
  10. dissolutionThe crude product is dissolved in Dichloromethane
  11. addition100 g of silica are added
  12. customthe solvent is evaporated
  13. additionThe resulting powder is added on top of 300 g of silica in a sintered glass funnel
  14. washthe product eluted with Hexane/Ethylacetate=8:1
  15. customThe product is crystallized from 2-Propanol

Sources & evidence

ORD record
ord-6c437c865f264842a4464ded9b704d09
Source dataset
uspto-grants-2014_04
Patent number
US08685541B2

Reaction notes

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