Hexane → HCID 85791306, compound

HRID 1444990Notes

Reaction equation

HRID 1444990 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].CCCCCC.C(C1C=[CH:25][C:24]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:16]=2[CH:15]=1)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[CH:4]([C:3]1[CH:2]=[CH:25][C:24]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:16]=2[CH:15]=1)=[CH2:5]

Participants

6

Reactant 3

HCID 8058HexaneHCID 12990116HCID 12990116, compoundHCID 178418339Butyllithium

Product 1

HCID 85791306HCID 85791306, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyltriphenylphosphonium bromide (714 mg, 2 mmol) in ether at 0° C. was added dropwise 1.6 M n-BuLi solution in hexane (1.25 mL, 2.00 mmol). The solution was stirred at 0° C. for 40 min and then was warmed to room temperature. A solution of 2-formyl-9,9-dioctylfluorene (585 mg, 1.4 mmol) was then added and reaction mixture was stirred overnight. The reaction mixture was quenched with 20 mL of 1% HCl. The mixture was extracted with ether and the organic layer was washed with NaHCO3 solution, and brine solution, and dried over MgSO4. The solvent was removed in vacuo and the product was purified by column chromatography on silica gel using hexane as the elutant to afford the purified 2-vinyl-9,9-dioctylfluorene (0.2834 g, 49% yield). EI-MS: 416 (M+), 360,192 (100). 1H NMR (CDCl3) δ 7.66 (m, 2H), 7.42-7.32 (m, 5H), 6.83 (dd, 1H), 5.82 (d, 1H), 5.28 (d, 1H), 1.97 (m, 4H), 1.28-1.06 (m, 22H), 0.83 (t, 5H), 0.63 (t, 3H). 13C NMR (CDCl3) δ151.09, 151.00, 141.08, 140.8, 137.51, 136.47, 127.05, 126.77, 125.21, 122.88, 120.54, 119.69 (2C), 112.89, 54.97, 40.39, 31.84, 31.65, 30.09, 29.25, 23.75, 22.65, 14.10

Workup

  1. temperaturewas warmed to room temperature
  2. customreaction mixture
  3. stirringwas stirred overnight
  4. customThe reaction mixture was quenched with 20 mL of 1% HCl
  5. extractionThe mixture was extracted with ether
  6. washthe organic layer was washed with NaHCO3 solution, and brine solution
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed in vacuo
  9. customthe product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-112e53708feb4927b04693afa3cb2d7e
Source dataset
uspto-grants-2010_02
Patent number
US07663301B2

Reaction notes

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