Propargyl bromide → HCID 59400689, compound

HRID 661775Notes

Reaction equation

HRID 661775 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[CH2:5]([C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([CH2:14][CH3:15])[C:8]=1[CH:16]1[C:26](=[O:27])[CH2:25][C:19]2([CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH2:18][C:17]1=[O:28])[CH3:6].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:5]([C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([CH2:14][CH3:15])[C:8]=1[C:16]1[C:26](=[O:27])[CH2:25][C:19]2([CH2:18][C:17]=1[O:28][CH2:3][C:2]#[CH:1])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH3:6]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 68468810HCID 68468810, compound

Product 1

HCID 59400689HCID 59400689, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of propargyl bromide (0.043 g, 0.36 mmol) in acetone (2 ml) is added dropwise to a mixture of 9-(2,6-diethyl-4-methylphenyl)-3-oxaspiro[5.5]undecane-8,10-dione (0.10 g, 0.3 mmol) and potassium carbonate (0.05 g, 0.36 mmol) in acetone (3 ml) and the reaction is refluxed overnight. The solvent is evaporated in vacuo, and the residue is taken up in ethyl acetate and washed with 2 N aqueous sodium hydroxide solution. The organic phase is concentrated in vacuo, and the residue is further purified by column chromatography on silica gel to give the desired compound as a colourless gum.

Workup

  1. temperaturethe reaction is refluxed overnight
  2. customThe solvent is evaporated in vacuo
  3. washwashed with 2 N aqueous sodium hydroxide solution
  4. concentrationThe organic phase is concentrated in vacuo
  5. customthe residue is further purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-711ef01b2fd44ec1a61bd7dc46ab92cf
Source dataset
uspto-grants-2011_12
Patent number
US08084649B2

Reaction notes

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