Hydrochloric Acid → α-Formyl-2-thiopheneacetonitrile

HRID 1844332Notes

Reaction equation

HRID 1844332 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]#[N:8].N#N.[O-:11][CH2:12]C.[Na+].C(OCC)=O.Cl>C(O)C.O>[O:11]=[CH:12][CH:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C:7]#[N:8]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 8025Ethyl formateHCID 728802-ThienylacetonitrileHCID 2723922Sodium ethoxide

Product 1

HCID 10464503α-Formyl-2-thiopheneacetonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Thiophen-2-yl-acetonitrile [20893-30-5] (6.7 mL, 62.6 mmol) was added to a N2 blanketed, 0° C., stirred solution of 21 wt % sodium ethoxide (25.7 mL, 68.9 mmol) in ethanol (100 mL). After 5 minutes, ethyl formate [109-94-4] (12.6 mL, 156.7 mmol) was added and the resultant solution was stirred for 20 minutes. The ice bath was then removed and replaced with a heating mantle. The reaction was heated to reflux for 2 h, cooled, and evaporated to provide a yellow solid. Crude product was dissolved in water, the solution chilled to 0° C. and acidified with aqueous hydrochloric acid to precipitate an off white powder. Product was isolated by filtration, washed with water, and dried to afford 7.4 g. LRMS (ESI) m/z 152.0 [(M+H)]+, calc'd for C7H6NOS: 151.19

Workup

  1. customblanketed, 0° C.
  2. customThe ice bath was then removed
  3. temperatureThe reaction was heated
  4. temperatureto reflux for 2 h
  5. temperaturecooled
  6. customevaporated
  7. customto provide a yellow solid
  8. customto precipitate an off white powder
  9. customProduct was isolated by filtration
  10. washwashed with water
  11. customdried
  12. customto afford 7.4 g

Sources & evidence

ORD record
ord-b8b361c5f4ea4e7692163acbe8401414
Source dataset
uspto-grants-2015_02
Patent number
US08946415B2

Reaction notes

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