Imidazole → Triethyl[(4-methyloct-1-yn-4-yl)oxy]silane

HRID 1649053Notes

Reaction equation

HRID 1649053 reaction equation
[OH:1][C:2]([CH3:10])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5].N1C=CN=C1.[CH2:16]([Si:18]([CH2:22][CH3:23])([CH2:20][CH3:21])Cl)[CH3:17]>CN(C)C=O>[CH3:10][C:2]([O:1][Si:18]([CH2:22][CH3:23])([CH2:20][CH3:21])[CH2:16][CH3:17])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 109096581-Octyn-4-ol, 4-methyl-

Product 1

HCID 13260212Triethyl[(4-methyloct-1-yn-4-yl)oxy]silaneYield 94.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 175.8 g of 4-hydroxy-4-methyl-1-octyne (U.S. Pat. No. 4,233,231 ), 112.1 g of imidazole and 625 ml of dry dimethylformamide (DMF) was stirred under dry nitrogen and 207.9 g of triethylchlorosilane added. The resulting homogenous solution was stirred at 50°-55° for 19 hours, then cooled to 25° C. and partitioned between hexane and water. The hexane layer was washed three times with water, then dried over anhydrous magnesium sulfate (MgSO4), and hexane evaporated in vacuo. The concentrate was distilled to yield 94.7% of the title compound as a colorless liquid, bp 60°-61° C. (0.20 mm Hg).

Workup

  1. custompartitioned between hexane and water
  2. washThe hexane layer was washed three times with water
  3. dry with materialdried over anhydrous magnesium sulfate (MgSO4), and hexane
  4. customevaporated in vacuo
  5. distillationThe concentrate was distilled

Sources & evidence

ORD record
ord-f2f3d3ab7cb94015a4f2dd1eaf0ffba7
Source dataset
uspto-grants-1983_11
Patent number
US04415501

Reaction notes

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