Imidazole → 2-(Prop-2-yn-1-yl)-4-[(triethylsilyl)oxy]cyclopent-2-en-1-one

HRID 483269Notes

Reaction equation

HRID 483269 reaction equation
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][C:9]#[CH:10])=[CH:3]1.N1C=CN=C1.[CH2:16]([Si:18](Cl)([CH2:21][CH3:22])[CH2:19][CH3:20])[CH3:17]>CN(C)C=O.O>[CH2:8]([C:4]1[C:5](=[O:7])[CH2:6][CH:2]([O:1][Si:18]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:16][CH3:17])[CH:3]=1)[C:9]#[CH:10]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 13037859HCID 13037859, compound

Product 1

HCID 135191972-(Prop-2-yn-1-yl)-4-[(triethylsilyl)oxy]cyclopent-2-en-1-oneYield 80.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 250 mg (1.84 mmole) of the title compound of Example B in 4 ml of dimethylformamide was treated successively with 200 mg (3 mmole) of imidazole and 300 mg (2 mmole) of triethylsilyl chloride. After stirring for thirty minutes, the reaction mixture was diluted with water, washed with diethyl ether, dried over sodium sulfate, filtered, and concentrated to dryness. The crude material was chromatographed on silica gel to give 0.37 g of the title compound as an oil. Structure assignment was confirmed by the proton nmr spectrum: 2.13 (t, J=2 Hz, ≡C--H), 3.08 (mult, --CH2 --C≡), 4.90 (mult C-11), ##STR9##

Workup

  1. washwashed with diethyl ether
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude material was chromatographed on silica gel

Sources & evidence

ORD record
ord-cc49823c87cd47629fdb278812d63f0c
Source dataset
uspto-grants-1986_03
Patent number
US04578505

Reaction notes

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