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

HRID 1448361Notes

Reaction equation

HRID 1448361 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 597), 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 liquor, p.m.r. spectrum, δ 1.26 (singlet, 3, CH3), 1.92 (triplet, 1, HC≡), 2.30 (doublet, 2, CH2).

Workup

  1. additionthe mixture is poured into 800 ml
  2. washThe mixture is washed thoroughly with water
  3. dry with materialThe solution is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a liquor, p.m.r

Sources & evidence

ORD record
ord-75e38e703ef442b79d6be7be44feabd8
Source dataset
uspto-grants-1979_12
Patent number
US04179451

Reaction notes

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