Potassium Carbonate → 5-Butoxy-2-cyanothiophen-3-yl dimethyl phosphate

HRID 263036

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[P:7](Cl)([O:11][CH3:12])([O:9][CH3:10])=[O:8].[C:14]([C:16]1[S:17][C:18]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:19][C:20]=1[OH:21])#[N:15]>C(#N)C>[C:14]([C:16]1[S:17][C:18]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:19][C:20]=1[O:21][P:7]([O:11][CH3:12])([O:9][CH3:10])=[O:8])#[N:15]

Participants

Conditions

Temperature: 20 °C

Procedure

7.7 g of potassium carbonate and 7.7 g of O,O-dimethyl chlorophosphate were added to a solution of 11 g of 2-cyano-3-hydroxy-5-n-butoxy-thiophene in 150 ml of acetonitrile and the mixture was stirred for 16 hours at 20° C. and was filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was dissolved in ether. The ether solution was washed with water containing 100 g/l of sodium chloride and then with 0.1 N sodium hydroxide solution containing 100 g/l of sodium chloride. The ether phase was dried and treated with activated carbon, filtered and concentrated to dryness to obtain 12.5 g of 2-cyano-3-(dimethoxyphosphoryloxy)-5-n-butoxy-thiophene with a refractive index of nD20 =1.511.

Workup

filtrationwas filtered
customThe filtrate was evaporated to dryness under reduced pressure
dissolutionthe residue was dissolved in ether
washThe ether solution was washed with water containing 100 g/l of sodium chloride
additionwith 0.1 N sodium hydroxide solution containing 100 g/l of sodium chloride
dry with materialThe ether phase was dried
additiontreated with activated carbon
filtrationfiltered
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-1928049dd38644a09c5790389ad6f9ba
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04155996

Linked notes

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