Hexane → 2-(3-Tert-butylcyclopentadienyl)-2-(1,1,4,4,7,7,10,10-octamethyl-1,2,3,4,7,8,9,10-octahydrodibenzo(b,h)-fluorenyl)propane

HRID 270991Notes

Reaction equation

HRID 270991 reaction equation
[CH3:1][C:2]1([CH3:29])[C:18]2[CH:17]=[C:16]3[C:8]([C:9]4[CH:10]=[C:11]5[C:22]([CH3:24])([CH3:23])[CH2:21][CH2:20][C:19]([CH3:26])([CH3:25])[C:12]5=[CH:13][C:14]=4[CH2:15]3)=[CH:7][C:6]=2[C:5]([CH3:28])([CH3:27])[CH2:4][CH2:3]1.CCCCCC.C([Li])CCC.[C:41]([C:45]1[CH:46]=[CH:47][C:48](=[C:50]([CH3:52])[CH3:51])[CH:49]=1)([CH3:44])([CH3:43])[CH3:42]>C1COCC1.O>[C:41]([C:45]1[CH:46]=[CH:47][CH:48]([C:50]([CH:20]2[CH2:21][C:22]([CH3:24])([CH3:23])[C:11]3[CH:10]=[C:9]4[C:14](=[CH:13][C:12]=3[C:19]2([CH3:26])[CH3:25])[CH2:15][C:16]2[CH:17]=[C:18]3[C:2]([CH3:29])([CH3:1])[CH2:3][CH2:4][C:5]([CH3:28])([CH3:27])[C:6]3=[CH:7][C:8]4=2)([CH3:52])[CH3:51])[CH:49]=1)([CH3:44])([CH3:43])[CH3:42]

Participants

7

Reactant 4

HCID 8058HexaneHCID 126031611,1,4,4,7,7,10,10-Octamethyl-2,3,4,7,8,9,10,12-octahydro-1H-dibenzo[b,h]fluoreneHCID 146882832-tert-Butyl-5-(propan-2-ylidene)cyclopenta-1,3-dieneHCID 178418339Butyllithium

Product 1

HCID 1317251232-(3-Tert-butylcyclopentadienyl)-2-(1,1,4,4,7,7,10,10-octamethyl-1,2,3,4,7,8,9,10-octahydrodibenzo(b,h)-fluorenyl)propaneYield 43.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.55 g (4.0 mmol) of 1,1,4,4,7,7,10,10-octamethyl-1,2,3,4,7,8,9,10-octahydrodibenzo(b,h)-fluorene in 50 ml of THF, 2.6 ml (4.2 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 0.97 g (6.0 mmol) of 3-tert-butyl-6,6-dimethylfulvene in 25 ml of THF was further dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. Then, 60 ml of water was added. The organic phase extracted with ether and separated was dried over magnesium sulfate and then filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid was purified by column chromatography (silica gel, developing solvent: hexane) to obtain 0.95 g of a light yellow solid (yield: 43%). The analyzed values are given below.

Workup

  1. stirringby stirring at room temperature for one night
  2. extractionThe organic phase extracted with ether
  3. customseparated
  4. dry with materialwas dried over magnesium sulfate
  5. filtrationfiltered
  6. customFrom the filtrate, the solvent was removed under reduced pressure
  7. customto obtain a solid
  8. customThe solid was purified by column chromatography (silica gel, developing solvent: hexane)

Sources & evidence

ORD record
ord-25a1a088cf5d455482773471fe9e5e52
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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