Imidazole → Silane, trimethyl[[1-methyl-1-(2-propynyl)pentyl]oxy]-

HRID 1395157Notes

Reaction equation

HRID 1395157 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.CN(C)C=O.Cl[Si:22]([CH3:25])([CH3:24])[CH3:23]>CCCCCC>[CH3:10][C:2]([O:1][Si:22]([CH3:25])([CH3:24])[CH3:23])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 109096581-Octyn-4-ol, 4-methyl-

Product 1

HCID 10856810Silane, trimethyl[[1-methyl-1-(2-propynyl)pentyl]oxy]-

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a stirred solution of 75.4 g (0.537 moles) of 4-hydroxy-4-methyl-1-octyne (Example 122), 104.9 g (1.54 moles) of imidazole, and 325 ml of dimethylformamide is added 65.2 g (0.60 moles) of chlorotrimethylsilane. After standing overnight the mixture is poured into 800 ml of hexane. The mixture is washed thoroughly with water followed by sodium bicarbonate solution and brine. The solution is dried over magnesium sulfate, filtered, and evaporated to give a liquid, p.m.r spectrum, δ 1.26 (singlet, 3, CH3), 1.92 (triplet, 1, HC), 2.30 (doublet, 2, CH2).

Workup

  1. washThe mixture is washed thoroughly with water
  2. dry with materialThe solution is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto give a liquid, p.m.r spectrum, δ 1.26 (singlet, 3, CH3), 1.92 (triplet, 1, HC), 2.30 (doublet, 2, CH2)

Sources & evidence

ORD record
ord-ff1848261a7f483fb349b19b46a4f693
Source dataset
uspto-grants-1980_05
Patent number
US04202822

Reaction notes

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