Methanol → HCID 131725137, compound

HRID 495760Notes

Reaction equation

HRID 495760 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].[CH3:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[CH2:28]([Li])[CH2:29][CH2:30][CH3:31].CO>C1COCC1.CCOCC.O>[C:24]1([C:30]([CH:29]2[CH:28]=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:17]2)([C:11]2[C:10]3[CH2:9][C:8]4[C:16](=[CH:17][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=4)[C:15]=3[CH:14]=[C:13]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=2)[CH3:31])[CH:23]=[CH:22][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 8058HexaneHCID 111404373,6-DI-Tert-butylfluoreneHCID 178418339Butyllithium

Product 1

HCID 131725137HCID 131725137, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.92 g (6.9 mmol) of 3,6-di-tert-butylfluorene in 30 ml of THF, 4.4 ml (7.2 mmol) of a hexane solution of n-butyllithium was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. To the resulting red solution, a solution of 1.70 g (7.6 mmol) of 3-tert-butyl-6,6-methylphenylfulvene in 40 ml of THF was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. After the reaction solution was diluted with 100 ml of ether, 50 ml of water was added. The separated organic phase was washed with water and a saturated saline solution, then dried over magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid was reslurried with 50 ml of methanol, and the resulting slurry was filtered to obtain 1.0 g (1.99 mmol) of a white solid (yield: 29%). The analyzed values are given below.

Workup

  1. stirringby stirring at room temperature for one night
  2. additionwas added
  3. washThe separated organic phase was washed with water
  4. dry with materiala saturated saline solution, then dried over magnesium sulfate
  5. filtrationfiltered
  6. customFrom the filtrate, the solvent was removed under reduced pressure
  7. customto obtain a solid
  8. filtrationthe resulting slurry was filtered

Sources & evidence

ORD record
ord-3b69eb04dafb4e21a4d4cfb064cdc456
Source dataset
uspto-grants-2005_09
Patent number
US06939928B1

Reaction notes

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