2-Thiophenecarboxaldehyde → HCID 9926157, compound

HRID 1604736Notes

Reaction equation

HRID 1604736 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7].[N+:8]([O-:11])([O-])=[O:9].[K+].[CH2:13]([O:15][P:16]([O-:20])[O:17][CH2:18][CH3:19])[CH3:14]>S(=O)(=O)(O)O>[N+:8]([C:4]1[CH:3]=[C:2]([CH:6]([P:16](=[O:20])([O:17][CH2:18][CH3:19])[O:15][CH2:13][CH3:14])[OH:7])[S:1][CH:5]=1)([O-:11])=[O:9]

Participants

5

Reactant 3

HCID 73642-ThiophenecarboxaldehydeHCID 24434Potassium NitrateHCID 3780918Diethylphosphite

Product 1

HCID 9926157HCID 9926157, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Thiophene-2-carboxaldehyde (3.20 mL, 34.0 mmol) was dissolved in sulfuric acid (20 mL) and cooled to 0° C. Potassium nitrate (4.05 g, 44.0 mmol) was added and the resultant mixture was stirred for 30 minutes and was poured onto ice. The product was extracted with ether, washed with aqueous sodium bicarbonate, dried with anhyrous magnesium sulfate and evaporated to give an oil which was immediately mixed with diethylphosphite (4.40 mL, 34.0 mmol) and adsorbed onto excess basic alumina. After 18 hours, the product was extracted with methylene chloride, concentrated in vacuo to an oil and purified by column chromatography (silica gel) with ethyl acetate-hexane 1:1 to give 1.01 g (10.0%) as an oil. 1H NMR (DMSO-D6): d, 8.64 (s,1H) 7.62 (s,1H) 6.95 (dd,1H,OH), 5.36 (dd,1H,PCH), 4.05 (m,4H,CH2), 1.22 (t,6H,CH3). MS (DCl): 296 (MH+), 278 (M-OH). C9H14NO6PS.

Workup

  1. additionwas poured onto ice
  2. extractionThe product was extracted with ether
  3. washwashed with aqueous sodium bicarbonate
  4. dry with materialdried with anhyrous magnesium sulfate
  5. customevaporated
  6. customto give an oil which
  7. extractionthe product was extracted with methylene chloride
  8. concentrationconcentrated in vacuo to an oil
  9. custompurified by column chromatography (silica gel) with ethyl acetate-hexane 1:1
  10. customto give 1.01 g (10.0%) as an oil

Sources & evidence

ORD record
ord-151da8c1d8f340d98c13846d94661440
Source dataset
uspto-grants-1999_11
Patent number
US05994563

Reaction notes

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