Sodium Cyanide → HCID 178455453, compound

HRID 1063637Notes

Reaction equation

HRID 1063637 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:21])([CH3:20])[C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14]OS(C)(=O)=O)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C-:22]#[N:23].[Na+]>CN(C=O)C>[C:1]([SiH2:5][O:6][C:7]([CH3:21])([CH3:20])[C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][C:22]#[N:23])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 178455455HCID 178455455, compound

Product 1

HCID 178455453HCID 178455453, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

38.2 g of crude trans-methanesulfonic acid 4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexylmethyl ester and 16.7 g (340 mmol, 3.2 eq) of sodium cyanide dissolved in 380 mL of DMF were stirred at 80° C. for 2 h. After cooling the reaction mixture down to RT, it was partitioned between ether and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure and the residue was then purified by chromatography on silica gel with a 9:1 v/v mixture of n-hexane and EtOAc as the eluent giving 24.2 g (80% over two steps) of pure trans-[4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-acetonitrile as colorless viscous oil, MS: 290 (MNa+).

Workup

  1. temperatureAfter cooling the reaction mixture down to RT, it
  2. customwas partitioned between ether and water
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was then purified by chromatography on silica gel with a 9:1 v/v mixture of n-hexane and EtOAc as the eluent

Sources & evidence

ORD record
ord-a35c9416191242babb35c208b3f0296b
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

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