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

HRID 65590

Reaction equation

HRID 65590 reaction equation
C(=O)([O-])[O-].[K+].[K+].[P:7](Cl)([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])=[O:8].[C:16]([C:18]1[S:19][C:20]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:21][C:22]=1[OH:23])#[N:17]>C(#N)C>[C:16]([C:18]1[S:19][C:20]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:21][C:22]=1[O:23][P:7]([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])=[O:8])#[N:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13139Diethyl chlorophosphateHCID 213179005-Butoxy-3-hydroxythiophene-2-carbonitrile

Product 1

HCID 213179365-Butoxy-2-cyanothiophen-3-yl diethyl phosphateYield 93.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7.7 g of potassium carbonate and 8.6 g of O,O-diethyl 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 room temperature and was then filtered. The filtrate was evaporated to dryness and the residue was taken up in ethyl ether. The ether phase was washed with an aqueous solution of 100 g/l of sodium chloride and then with an aqueous 0.1N sodium hydroxide solution containing 100 g/l of sodium chloride. The solution was dried, treated with activated carbon, filtered and evaporated to dryness under reduced pressure to obtain 15.5 g of 2-cyano-3-(diethoxyphosphoryloxy)-5-n-butoxy-thiophene with a refractive index of nD20 = 1.500.

Workup

  1. filtrationwas then filtered
  2. customThe filtrate was evaporated to dryness
  3. washThe ether phase was washed with an aqueous solution of 100 g/l of sodium chloride
  4. additionwith an aqueous 0.1N sodium hydroxide solution containing 100 g/l of sodium chloride
  5. customThe solution was dried
  6. additiontreated with activated carbon
  7. filtrationfiltered
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e7487320950f418a9e636fd700ecdb7c
Source dataset
uspto-grants-1978_12
Patent number
US04128562

Linked notes

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