Hexane → (6-(4-Fluorophenyl)hexa-1,5-diynyl)trimethylsilane
Reaction equation
[CH2:1]([Si:3]([CH2:9]C)([CH2:7]C)[C:4]#[C:5][CH3:6])C.[Li]CCCC.CCCCCC.Br[CH2:23][C:24]#[C:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1>C1COCC1>[F:32][C:29]1[CH:30]=[CH:31][C:26]([C:25]#[C:24][CH2:23][CH2:6][C:5]#[C:4][Si:3]([CH3:1])([CH3:7])[CH3:9])=[CH:27][CH:28]=1Participants
6
Conditions
- Temperature
- -78 °C
Procedure
To a solution of triethyl(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 stirring 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 1 h 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
- stirringthe resulting mixture was stirred for 1 h at −78° C.
- temperaturewarmed to room temperature for an additional 1 h
- customThe reaction mixture was quenched with water
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b7166ec1524f4363966446353459ddaa
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101637B2
Reaction notes
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