Water → (6-Chlorohex-1-yn-1-yl)trimethylsilane

HRID 1494664Notes

Reaction equation

HRID 1494664 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C([Li])CCC.[Cl:12][CH2:13][CH2:14][CH2:15][CH2:16]I.O>O1CCCC1>[Cl:12][CH2:13][CH2:14][CH2:15][CH2:16][C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 66111TrimethylsilylacetyleneHCID 825271-Chloro-4-iodobutaneHCID 178418339Butyllithium

Product 1

HCID 13839479(6-Chlorohex-1-yn-1-yl)trimethylsilane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of trimethylsilylacetylene (4.9 g., Aldrich) in dry tetrahydrofuran (40 ml.) was stirred at 0° under a current of nitrogen and n-butyllithium (31.25 ml. of 1.6M solution in hexane) was added dropwise. The solution was stirred for 30 minutes and a solution of 1-chloro-4-iodobutane (10.9 g.) in dry tetrahydrofuran (30 ml.) was added. The reaction mixture was allowed to warm to 20° and stirred for 18 hours. The mixture was poured into water and the aqueous mixture was extracted with diethyl ether. The ethereal extracts were washed with water and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo. 6-Chloro-1-trimethylsilylhex-1-yne was obtained as a yellow liquid and was used without further purification.

Workup

  1. additionwas added dropwise
  2. temperatureto warm to 20°
  3. stirringstirred for 18 hours
  4. extractionthe aqueous mixture was extracted with diethyl ether
  5. washThe ethereal extracts were washed with water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e3dfe52249bc4c5499376507bc2e3b7b
Source dataset
uspto-grants-1991_06
Patent number
US05026874

Reaction notes

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