Water → 1-Chloro-5-(trimethylsilyl)-4-pentyne

HRID 129318Notes

Reaction equation

HRID 129318 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]I.O>O1CCCC1>[Cl:12][CH2:13][CH2:14][CH2:15][C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 66111TrimethylsilylacetyleneHCID 813631-Chloro-3-iodopropaneHCID 178418339Butyllithium

Product 1

HCID 27579421-Chloro-5-(trimethylsilyl)-4-pentyne

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of trimethylsilylacetylene (12.0 g., Aldrich) in dry tetrahydrofuran (100 ml.) was stirred at 0°, under a current of nitrogen and n-butyllithium (76.5 ml. of 1.6M solution in hexane) was added dropwise. The solution was stirred for 30 minutes and a solution of 1-chloro-3-iodopropane (25.0 g.) in dry tetrahydrofuran (75 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 and the residue distilled. 5-Chloro-1-trimethylsilylpent-1-yne was obtained as a colourless oil (12.7 g., b.p. 67°-72°, 15 mm. Hg.).

Workup

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

Sources & evidence

ORD record
ord-fe195a21b77a4ef080d2a253843a836a
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Reaction notes

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