Chlorotrimethylsilane → HCID 19609254, compound

HRID 1603273Notes

Reaction equation

HRID 1603273 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][OH:6])#[CH:2].[CH3:11][Si:12](Cl)([CH3:14])[CH3:13]>C(N(CC)CC)C>[CH3:11][Si:12]([O:6][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=1[C:1]#[CH:2])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 11007947(2-Ethynylphenyl)methanol

Product 1

HCID 19609254HCID 19609254, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

970 mg of 2-ethynyl-benzyl alcohol were dissolved in 50 ml of diethyl ester. 1.9 ml of triethylamine was added, followed by dropwise addition of 0.9 ml of trimethylsilyl chloride. The reaction mixture was stirred at room temperature for 4 hours, poured onto ice/5% aqueous sodium bicarbonate and extracted with ether. The oily residue obtained after drying and evaporation of the solvent was distilled to give 1.3 g of 2-ethynylbenzyl trimethylsilyl ether as a colourless oil, b.p. 85-89° C./0.8 mm.

Workup

  1. additionpoured onto ice/5% aqueous sodium bicarbonate
  2. extractionextracted with ether
  3. customThe oily residue obtained
  4. customafter drying
  5. customevaporation of the solvent
  6. distillationwas distilled

Sources & evidence

ORD record
ord-42a66d4167f445be9732fc5d8a42acd9
Source dataset
uspto-grants-1999_11
Patent number
US05986131

Reaction notes

Loading…