Hydrochloric Acid → 2-ethyl-5-(tetrahydro-2H-pyran-4-yl)thiophene-3-carbaldehyde

HRID 1877209

Reaction equation

HRID 1877209 reaction equation
[CH2:1]([C:3]1[S:4][C:5]([CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:6][C:7]=1[C:8](OCC)=[O:9])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.Cl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])=O.[Na+].[Na+]>O1CCCC1.C1(C)C=CC=CC=1.C(Cl)Cl>[CH2:1]([C:3]1[S:4][C:5]([CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:6][C:7]=1[CH:8]=[O:9])[CH3:2]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 21225700DiisobutylaluminumhydrideHCID 68514211ethyl 2-ethyl-5-(tetrahydro-2H-pyran-4-yl)thiophene-3-carboxylate

Product 1

HCID 866463922-ethyl-5-(tetrahydro-2H-pyran-4-yl)thiophene-3-carbaldehydeYield 61.3%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution (20 mL) of ethyl 2-ethyl-5-(tetrahydro-2H-pyran-4-yl)thiophene-3-carboxylate (1.35 g) synthesized above in tetrahydrofuran was added 1.5M diisobutylaluminum hydride in toluene solution (15.1 mL) at 0° C., and the mixture was stirred for 1 hr. 1N Hydrochloric acid was added to quench the reaction, the organic solvent was evaporated using evaporator, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to give a colorless oil. To a solution of the obtained oil in methylene chloride (20 mL) was added Dess-Martin reagent (2.47 g), and the mixture was stirred at room temperature for 1.5 hr. Saturated aqueous sodium sulfite solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3, volume ratio) to give the title compound (692 mg, 61%) as a colorless oil.

Workup

  1. customto quench
  2. customthe reaction
  3. customthe organic solvent was evaporated
  4. customevaporator
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto give a colorless oil
  10. stirringthe mixture was stirred at room temperature for 1.5 hr
  11. customto quench
  12. customthe reaction
  13. extractionthe mixture was extracted with ethyl acetate
  14. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  15. dry with materialdried over magnesium sulfate
  16. concentrationconcentrated under reduced pressure
  17. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3, volume ratio)

Sources & evidence

ORD record
ord-090122576ff3461fb854b8de094e59a4
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Linked notes

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