Tetrahydrofuran → 9-allyl-9-((2E)-2-butenyl)-fluorene

HRID 2421459Notes

Reaction equation

HRID 2421459 reaction equation
[CH2:1]([CH:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:2]=[CH2:3].O1[CH2:21][CH2:20][CH2:19][CH2:18]1.C([Li])CCC.C(Cl)/C=C/C>O.CCCCCC>[CH2:1]([C:4]1([CH2:18]/[CH:19]=[CH:20]/[CH3:21])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[C:11]2[C:16]1=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 637923(2E)-1-Chloro-2-buteneHCID 124601409-allyl-9H-fluoreneHCID 178418339Butyllithium

Product 1

HCID 866233909-allyl-9-((2E)-2-butenyl)-fluorene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

There were put 2.5 g of 9-allylfluorene and 31.3 mL of dry tetrahydrofuran manufactured by Kanto Chemical Co., Inc. in a 100 mL-three necked flask. There were added dropwise thereto at 0° C. over 30 minutes 9 mL of a hexane solution of n-butyllithium (concentration: 1.6 M) manufactured by Kanto Chemical Co., Inc. The resultant mixture was stirred for 2 hours at room temperature, and then 1.4 mL of trans-crotyl chloride manufactured by Aldrich Chemical Company was added dropwise thereto at 0° C. The temperature of the mixture was raised gradually up to room temperature, and then the mixture was stirred for 6 hours at room temperature. Water was added to the reaction mixture, and the obtained mixture was subjected to extraction with ether. The extract was washed with water and with a saline solution in this order. The washed extract was dried over anhydrous magnesium sulfate manufactured by Nacalai Tesque, Inc. The dried extract was subjected to removal of the solvent by distillation, and the resultant liquid was distilled in vacuo, thereby obtaining 2.43 g of 9-allyl-9-((2E)-2-butenyl)-fluorene at 155° C. under 4 mmHg.

Workup

  1. additionThere were added dropwise
  2. additionwas added dropwise
  3. customat 0° C
  4. extractionthe obtained mixture was subjected to extraction with ether
  5. washThe extract was washed with water and with a saline solution in this order
  6. extractionThe washed extract
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. extractionThe dried extract
  9. customwas subjected to removal of the solvent by distillation
  10. distillationthe resultant liquid was distilled in vacuo

Sources & evidence

ORD record
ord-cc69aca3f6ec4c7792fad69982c69ee4
Source dataset
uspto-grants-2011_06
Patent number
US07956145B2

Reaction notes

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