Sodium Cyanide → HCID 178455453, compound

HRID 2118238Notes

Reaction equation

HRID 2118238 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. The residue was chromatographed 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 chromatographed on silica gel with a 9:1 v/v mixture of n-hexane and EtOAc as the eluent

Sources & evidence

ORD record
ord-4aa0f94afeb34f4f94b438d7db77c4d2
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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