Sodium Iodide → HCID 178455225, compound

HRID 1456355Notes

Reaction equation

CS(O[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:9][CH2:8]1)(=O)=O.[I-].[Na+].[C-:24]#[N:25].[Na+]>CN(C)C=O>[Si:15]([O:14][CH2:13][C@H:10]1[CH2:11][CH2:12][C@H:7]([CH2:6][C:24]#[N:25])[CH2:8][CH2:9]1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 110 °C

Procedure

In 100 ml of dry dimethylformamide were suspended 11.0 g of trans-4-methanesulfonyloxymethyl-1-t-butyldimethylsilyloxymethylcyclohexane, 5.87 g of sodium iodide and 1.92 g of sodium cyanide, and the mixture was stirred at 50° C. for 1 hour and 45 minutes and further at 110° C. for 45 minutes. The reaction mixture was poured into 100 ml of ice-water and the mixture was extracted with 300 ml of ether. The extracts were washed with an aqueous citric acid solution, an aqueous sodium chloride solution, an aqueous sodium bicarbonate solution and an aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography employing cyclohexane-ethyl acetate (20:1-5:1) as an eluting solvent to obtain 7.41 g of the desired compound as a colorless oil.

Workup

extractionthe mixture was extracted with 300 ml of ether
washThe extracts were washed with an aqueous citric acid solution
dry with materialan aqueous sodium chloride solution, an aqueous sodium bicarbonate solution and an aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-1c220579d0304c12a2130a8c37f16fe5
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05843973

Reaction notes

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