Dimethylformamide → HCID 11096896, compound

HRID 1931067Notes

Reaction equation

HRID 1931067 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C[C:15]([CH3:18])([O-])[CH3:16].[K+].CN(C)C=O.[CH2:25](Cl)[CH:26]=[CH2:27]>O.CCCCCC>[CH2:16]([C:12]1([CH2:27][CH:26]=[CH2:25])[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH:15]=[CH2:18]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6853FluoreneHCID 7850Allyl chloride2×HCID 23665647Potassium tert-butoxide2×

Product 1

HCID 11096896HCID 11096896, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

There were charged 10 g of fluorene manufactured by Wako Pure Chemical Industries, Ltd. and 10.1 g of potassium tert-butoxide manufactured by Sigma Aldrich Japan Co., Ltd. into a 200 mL round bottom flask, and then 120 mL of dehydrated N,N-dimethylformamide manufactured by Wako Pure Chemical Industries, Ltd. was added to the round bottom flask. While stirring the round bottom flask at 50° C. in an atmosphere of nitrogen, 5.86 mL of allyl chloride manufactured by Kanto Chemical Co., Inc. was added dropwise to the round bottom flask over 2 hours. The round bottom flask was stirred further for 8 hours at 50° C., and then 10.1 g of potassium tert-butoxide manufactured by Sigma Aldrich Japan Co., Ltd. was additionally added to the round bottom flask, and 5.86 mL of allyl chloride manufactured by Kanto Chemical Co., Inc. was additionally added dropwise to the round bottom flask over 2 hours. The round bottom flask was stirred at 50° C. overnight, thereby obtaining a reaction product. The reaction product was added to 900 mL of water to obtain a mixture, and then 300 mL of hexane was added to the mixture, thereby obtaining a mixture containing an organic phase a water phase. The organic phase was extracted with ether three times. The extract was washed with water four times. The washed extract was further washed with dilute hydrochloric acid and with water in this order. The washed extract (ether solution) was dried over anhydrous magnesium sulfate manufactured by Nacalai Tesque, Inc. The dried ether solution was subjected to solvent elimination by evaporation, and the remainder was distilled under a reduced pressure, thereby obtaining 12.8 g (yield: 86.4%) of 9,9-diallylfluorene as yellow oil at 90° C./4 mmHg.

Workup

  1. additionwas added to the round bottom flask
  2. additionwas added dropwise to the round bottom flask over 2 hours
  3. additionwas additionally added dropwise to the round bottom flask over 2 hours
  4. stirringThe round bottom flask was stirred at 50° C. overnight
  5. customobtaining a reaction product
  6. customto obtain a mixture
  7. customobtaining a mixture
  8. extractionThe organic phase was extracted with ether three times
  9. washThe extract was washed with water four times
  10. extractionThe washed extract
  11. washwas further washed with dilute hydrochloric acid and with water in this order
  12. extractionThe washed extract (ether solution)
  13. dry with materialwas dried over anhydrous magnesium sulfate
  14. customThe dried ether solution was subjected to solvent elimination by evaporation
  15. distillationthe remainder was distilled under a reduced pressure

Sources & evidence

ORD record
ord-ca9bb79775094373afe59a2c62fa4339
Source dataset
uspto-grants-2012_05
Patent number
US08188202B2

Reaction notes

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