Imidazole → 3-Triethylsilyloxy-1-octyne

HRID 1632691Notes

Reaction equation

HRID 1632691 reaction equation
[CH:1]#[C:2][CH:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].N1C=CN=C1.CN(C)C=O.Cl[Si:21]([CH2:26][CH3:27])([CH2:24][CH3:25])[CH2:22][CH3:23]>CCCCCC.O.C1C=CC=CC=1.C(OCC)(=O)C>[CH2:22]([Si:21]([CH2:26][CH3:27])([CH2:24][CH3:25])[O:9][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:2]#[CH:1])[CH3:23]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 131661-Octyn-3-olHCID 13819Chlorotriethylsilane

Product 1

HCID 126753463-Triethylsilyloxy-1-octyne

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolventHCID 22114717Water hexaneSolvent

Procedure

To a magnetically stirred solution of 50 g of 1-octyn-3-ol, 83 g of imidazole, and 500 ml of anhydrous dimethylformamide, cooled in an ice-water bath under an argon atmosphere, is slowly added 90 g of chlorotriethylsilane. After several minutes the reaction mixture is warmed to ambient temperature, and the progress of the reaction is monitored by tlc (1:4/ethyl acetate:benzene). On completion, the reaction mixture is poured into 500 ml of an iced mixture of 1:1 hexane-water. The organic phase is separated, washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The resulting oil is distilled to provide 83 g (bp 70°-72° C., 0.35 mm).

Workup

  1. customThe organic phase is separated
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. distillationThe resulting oil is distilled
  6. customto provide 83 g (bp 70°-72° C., 0.35 mm)

Sources & evidence

ORD record
ord-78e77a1046f64ce78d70bda9c79fbed9
Source dataset
uspto-grants-1984_10
Patent number
US04477388

Reaction notes

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