Trimethylsilyl cyanide → HCID 66618856, compound

HRID 406359Notes

Reaction equation

HRID 406359 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.C[Si]([C:17]#[N:18])(C)C.C(=O)(O)[O-].[Na+]>[I-].[Zn+2].[I-]>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([O:12][CH2:11][CH2:10][OH:9])[C:17]#[N:18])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 873062-(3-Bromophenyl)-1,3-dioxolaneHCID 516892Sodium Bicarbonate

Product 1

HCID 66618856HCID 66618856, compound

Reagents, catalysts & solvents 1

HCID 9883512zinc(II)iodideCatalyst

Procedure

Zinc iodide (50.6 mg) was added to a mixture of 2-(3-bromophenyl)-1,3-dioxolane (3 mL) and trimethylsilyl cyanide (2.49 mL), followed by stirring at room temperature for 1.5 hours. A saturated sodium bicarbonate aqueous solution was added to the reaction solution, followed by extraction with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Then, the resulting residue was purified by silica gel column chromatography (elution solvent:heptane:ethyl acetate=7:3→1:1) to obtain 3.93 g of the title compound. The property values of the compound are as follows.

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThen, the resulting residue was purified by silica gel column chromatography (elution solvent:heptane:ethyl acetate=7:3→1:1)

Sources & evidence

ORD record
ord-dbfbe9331be847d2aead74b60b7207f9
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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