Diethyl Ether → 4-Trimethylsilyl-3-butyn-1-ol

HRID 485508Notes

Reaction equation

HRID 485508 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].CCOCC.C([Li])CCC.[CH3:16][Si:17]([CH3:20])([CH3:19])Cl>CCCCCC.O>[CH3:16][Si:17]([CH3:20])([CH3:19])[C:4]#[C:3][CH2:2][CH2:1][OH:5]

Participants

7

Reactant 4

HCID 3283Diethyl Ether2×HCID 6397ChlorotrimethylsilaneHCID 135663-Butyn-1-OLHCID 178418339Butyllithium

Product 1

HCID 27608274-Trimethylsilyl-3-butyn-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

A solution of 33.25 parts of 3-butyn-1-ol in 500 parts by volume ether is cooled to -60° C. under argon and treated dropwise with 400 parts by volume of a 2.5 molar solution of n-butyl lithium in hexane. One hour after the addition is complete, a solution of 130 parts by volume of trimethylchlorosilane in 130 parts by volume of ether is added dropwise. After the addition is complete, the temperature is allowed to rise to 0°. The reaction mixture is poured into water, washed with 1NHCl 3 times, additional water, dried over sodium sulfate and evaporated to a liquid which is distilled under water aspirator pressure to give 4-trimethylsilyl-3-butyn-1-ol, bp. 75-77 (13 Tor).

Workup

  1. additionOne hour after the addition
  2. additionAfter the addition
  3. customto rise to 0°
  4. washwashed with 1NHCl 3 times, additional water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to a liquid which
  7. distillationis distilled under water aspirator pressure

Sources & evidence

ORD record
ord-679edf2cf24d47e8bd6b7b517868f063
Source dataset
uspto-grants-1985_08
Patent number
US04536592

Reaction notes

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