Sodium Cyanide → 4,5-(Dimethylmethylenedioxy)-3-hydroxy-6-heptenenitrile

HRID 1741951Notes

Reaction equation

S([O-])([O-])(=O)=O.[Mg+2].[C-:7]#[N:8].[Na+].[O:10]1[CH:12]([CH:13]2[O:19][C:18]([CH3:21])([CH3:20])[O:17][CH:14]2[CH:15]=[CH2:16])[CH2:11]1>CO>[CH3:20][C:18]1([CH3:21])[O:17][CH:14]([CH:15]=[CH2:16])[CH:13]([CH:12]([OH:10])[CH2:11][C:7]#[N:8])[O:19]1

Participants

Conditions

Temperature: 10 °C

Procedure

Fifty milliliters of a saturated magnesium sulfate aqueous solution were cooled to 10° C., and 10.23 g of sodium cyanide was gradually added not to proceed over 10° C. After stirring at 10° C. for 45 minutes, a solution of 7.61 g of 1,2-epoxy-3,4-(dimethylmethylenedioxy)-5-hexene in 30 ml of methanol was gradually added to the above mixture not to proceed over 10° C. After stirring at room temperature for 2 hours, the reaction mixture was extracted with ethyl acetate. The extract was washed with a sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to afford 2.11 g of 4,5-(dimethylmethylenedioxy)-3-hydroxy-6-heptenenitrile having the following properties.

Workup

customto proceed over 10° C
customto proceed over 10° C
stirringAfter stirring at room temperature for 2 hours
extractionthe reaction mixture was extracted with ethyl acetate
washThe extract was washed with a sodium chloride aqueous solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-19f527fb225e47e58d7e13763e4dfa27
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05334740

Reaction notes

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