Hexane → HCID 131725134, compound

HRID 271017Notes

Reaction equation

HRID 271017 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]1([C:47]2[CH:48]=[CH:49][C:50](=[C:52]([C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)[C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[CH:51]=2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1COCC1.O>[C:41]1([C:47]2[CH:48]=[CH:49][CH:50]([C:52]([C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)([C:59]3[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=3)[CH:20]3[CH2:21][C:22]([CH3:24])([CH3:23])[C:11]4[CH:10]=[C:9]5[C:14](=[CH:13][C:12]=4[C:19]3([CH3:26])[CH3:25])[CH2:15][C:16]3[CH:17]=[C:18]4[C:2]([CH3:29])([CH3:1])[CH2:3][CH2:4][C:5]([CH3:28])([CH3:27])[C:6]4=[CH:7][C:8]5=3)[CH:51]=2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

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 223278143,6,6-TriphenylfulveneHCID 178418339Butyllithium

Product 1

HCID 131725134HCID 131725134, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.0 g (2.59 mmol) of 1,1,4,4,7,7,10,10-octamethyl-1,2,3,4,7,8,9,10-octahydrodibenzo(b,h)-fluorene in 30 ml of THF, 1.75 ml (2.85 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 4 hours. Then, a solution of 0.92 g (3.11 mmol) of 3,6,6-triphenylfulvene in 10 ml of THF was slowly added at room temperature, followed by stirring for 15 hours. To the reaction solution, 20 ml of water was added to terminate the reaction. The resulting solution was subjected to extraction with diethyl ether, then dried over anhydrous magnesium sulfate and vacuum evaporated to dryness to obtain a yellow solid. The solid was washed twice with a small amount of methanol and dried under reduced pressure to obtain 1.24 g of an opaque white solid (yield: 69.1%).

Workup

  1. stirringby stirring for 15 hours
  2. customto terminate
  3. customthe reaction
  4. extractionThe resulting solution was subjected to extraction with diethyl ether
  5. dry with materialdried over anhydrous magnesium sulfate and vacuum
  6. customevaporated to dryness
  7. customto obtain a yellow solid
  8. washThe solid was washed twice with a small amount of methanol
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-d37be32a2b3e46f5bbc5eafdc6164090
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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