Hexane → (6-(4-Fluorophenyl)hexa-1,5-diynyl)trimethylsilane

HRID 1189081Notes

Reaction equation

HRID 1189081 reaction equation
[CH3:1][Si:2]([CH3:7])([CH3:6])[C:3]#[C:4][CH3:5].[Li]CCCC.CCCCCC.Br[CH2:20][C:21]#[C:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1>C1COCC1>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:22]#[C:21][CH2:20][CH2:5][C:4]#[C:3][Si:2]([CH3:7])([CH3:6])[CH3:1])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 803631-(Trimethylsilyl)prop-1-yneHCID 105605241-(3-Bromoprop-1-yn-1-yl)-4-fluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 66597810(6-(4-Fluorophenyl)hexa-1,5-diynyl)trimethylsilaneYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of trimethyl(prop-1-ynyl)silane (2.19 g, 19.50 mmol) in 22 mL of THF at −78° C., was added dropwise n-BuLi 2.5M in hexane (7.8 mL, 20 mmol). After stiffing 2 hours at −78° C., 1-(3-bromoprop-1-ynyl)-4-fluorobenzene (1.40 g, 6.5 mmol) in 6 mL of THF was slowly added and the resulting mixture was stirred for 1h at −78° C. and warmed to room temperature for an additional 1 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered and concentrated to afford 1.57 g of (6-(4-fluorophenyl)hexa-1,5-diynyl)trimethylsilane (99%) as a yellow oil.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d6a422899f344861bdcab859496569a7
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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