Water → 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 495732Notes

Reaction equation

HRID 495732 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.C([Li])CCC.[C:35]([C:39]1[CH:40]=[CH:41][C:42](=[C:44]([CH3:46])[CH3:45])[CH:43]=1)([CH3:38])([CH3:37])[CH3:36].O>C1COCC1.CCCCCC>[C:35]([C:39]1[CH:40]=[CH:41][CH:42]([C:44]([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)([CH3:46])[CH3:45])[CH:43]=1)([CH3:38])([CH3:37])[CH3:36]

Participants

7

Reactant 4

HCID 962WaterHCID 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 8058HexaneCatalystHCID 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-4b18357dbd7e40f892dcf9cbe59dc060
Source dataset
uspto-grants-2005_09
Patent number
US06939928B1

Reaction notes

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