Sodium Cyanide → HCID 178455453, compound

HRID 967149Notes

Reaction equation

HRID 967149 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)C=O>[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 79.7%

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) of sodium cyanide dissolved in 380 ml of N,N-dimethylformamide were stirred for 2 hours at 80° C. After cooling the reaction mixture down to room temperature, it was partitioned between ether and water. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure and the residue then chromatographed on silica gel with a 9:1 v/v mixture of hexane and ethylacetate as the eluent giving 24.2 g (79.7% 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 room temperature, it
  2. customwas partitioned between ether and water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe residue then chromatographed on silica gel with a 9:1 v/v mixture of hexane and ethylacetate as the eluent

Sources & evidence

ORD record
ord-d4bb0333e3e44370b52c76641d7418c8
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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