Hexane → HCID 131725139, compound

HRID 271023Notes

Reaction equation

HRID 271023 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[CH2:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:12][CH:11]=3)([CH3:4])([CH3:3])[CH3:2].CCCCCC.[Li]CCCC.[CH:33]1([CH:39]=[C:40]2[CH:44]=[CH:43][CH:42]=[CH:41]2)[CH2:38][CH2:37][CH2:36][CH2:35]C1>C1COCC1>[CH:40]1([C:39]2([C:11]3[C:10]4[CH2:9][C:8]5[C:16](=[CH:17][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=5)[C:15]=4[CH:14]=[C:13]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=3)[CH2:35][CH2:36][CH2:37][CH2:38][CH2:33]2)[CH:41]=[CH:42][CH:43]=[CH:44]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 111404373,6-DI-Tert-butylfluoreneHCID 13250204HCID 13250204, compoundHCID 178418339Butyllithium

Product 1

HCID 131725139HCID 131725139, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 200 ml two-necked flask purged with nitrogen, 1.96 g (7.04 mmol, 1 eq) of 3,6-di-tert-butylfluorene was placed at room temperature. Then, 40 ml of dehydrated THF was added, and the mixture was stirred by a magnetic stirrer to give a solution. The solution was cooled with an ice bath (colorless transparent solution). To the solution, 5.0 ml (8.15 mmol, 1.16 eq) of a hexane solution of n-BuLi was dropwise added over a period of 5 minutes. Then, the ice bath was removed, and the solution was stirred at room temperature for 21 hours (red solution). After the solution was cooled with an ice bath, a solution of 1.37 g (9.37 mmol, 1.33 eq) of 6-cyclohexylfulvene in 5 ml of dehydrated THF was dropwise added over a period of 10 minutes. The ice bath was removed, and the solution was stirred at room temperature for 42 hours. The resulting brownish red solution was poured into 50 ml of a diluted hydrochloric acid solution to perform quenching. The soluble component was extracted from the aqueous layer with 100 ml of diethyl ether, and the organic phase was washed with 80 ml of a saturated saline solution. The dispensed organic phase was dried over MgSO4, then the MgSO4 was filtered off, and from the filtrate the solvent was vacuum distilled off by a rotary evaporator to obtain a brownish yellow solid. The solid was purified by silica gel column chromatography (developing solvent: hexane) to obtain 1.31 g of a white solid (yield: 44%).

Workup

  1. customwas placed at room temperature
  2. customto give a solution
  3. temperatureThe solution was cooled with an ice bath (colorless transparent solution)
  4. customThen, the ice bath was removed
  5. stirringthe solution was stirred at room temperature for 21 hours (red solution)
  6. temperatureAfter the solution was cooled with an ice bath
  7. customThe ice bath was removed
  8. stirringthe solution was stirred at room temperature for 42 hours
  9. additionThe resulting brownish red solution was poured into 50 ml of a diluted hydrochloric acid solution
  10. customto perform quenching
  11. extractionThe soluble component was extracted from the aqueous layer with 100 ml of diethyl ether
  12. washthe organic phase was washed with 80 ml of a saturated saline solution
  13. dry with materialThe dispensed organic phase was dried over MgSO4
  14. filtrationthe MgSO4 was filtered off
  15. distillationdistilled off by a rotary evaporator
  16. customto obtain a brownish yellow solid
  17. customThe solid was purified by silica gel column chromatography (developing solvent: hexane)

Sources & evidence

ORD record
ord-978c850c7cdc4b76aa688271e83848a3
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

Loading…