Sodium Cyanide → HCID 178455424, compound

HRID 133169Notes

Reaction equation

HRID 133169 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:18])([CH3:17])[C:8]1[CH2:9][CH:10]([CH2:14][CH:15]=O)[CH2:11][CH2:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].S([CH2:29][N+:30]#[C-:31])(C1C=CC(C)=CC=1)(=O)=O.[C-]#[N:33].[Na+]>C(O)C.N>[C:1]([SiH2:5][O:6][C:7]([CH3:18])([CH3:17])[C:8]1[CH2:9][CH:10]([CH2:14][C:15]2[N:33]=[CH:29][NH:30][CH:31]=2)[CH2:11][CH2:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 161915Tosylmethyl isocyanideHCID 131726104[3-(Tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enyl]-acetaldehyde2×

Product 1

HCID 178455424HCID 178455424, compoundYield 746.1%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

The aldehyde (Intermediate A5) (10 g, 37.2 mmol) in anhydrous ethanol (70 mL) was treated with tosylmethyl isocyanide (7.2 g, 3.7 mmol) (available from Aldrich) followed by addition of a catalytic amount of NaCN (150 mg) at rt for 15 m. The mixture was reduced in volume to about 20 mL under reduced pressure. The residue was dissolved in NH3 (7M in MeOH) and placed into re-sealable tubes and heated to 100° C. for 18 h. The mixture was cooled and the solvent removed under vacuum. The residue was purified by flash chromatography on silica gel with 5% MeOH:EtOAc to remove TsOH and the product was eluted with 5% NH3-MeOH in CH2Cl2 to yield 7 g (60%) of 4-[3-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enylmethyl]-1H-imidazole (Intermediate A6).

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent removed under vacuum
  3. customThe residue was purified by flash chromatography on silica gel with 5% MeOH
  4. customEtOAc to remove TsOH
  5. washthe product was eluted with 5% NH3-MeOH in CH2Cl2

Sources & evidence

ORD record
ord-db1cd03bc4394326a8a490f53a38c627
Source dataset
uspto-grants-2008_06
Patent number
US07390829B2

Reaction notes

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