Ethyl chloroformate → 6-tert-Butyl 2-ethyl 4,5-dihydrothieno[2,3-c]pyridine-2,6(7H)-dicarboxylate

HRID 2093101Notes

Reaction equation

HRID 2093101 reaction equation
[S:1]1[C:5]2[CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9][C:4]=2[CH:3]=[CH:2]1.C([Li])CCC.[CH2:22]([O:24][C:25](Cl)=[O:26])[CH3:23]>C1COCC1>[S:1]1[C:5]2[CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9][C:4]=2[CH:3]=[C:2]1[C:25]([O:24][CH2:22][CH3:23])=[O:26]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 17389936tert-butyl 4,5-Dihydrothieno[2,3-c]pyridine-6(7H)-carboxylateHCID 178418339Butyllithium

Product 1

HCID 581577296-tert-Butyl 2-ethyl 4,5-dihydrothieno[2,3-c]pyridine-2,6(7H)-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyl 4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate in dry THF was cooled to −78°, n-butyl lithium (1.5 eq.) was added slowly and reaction mixture stirred for 3-4 hrs. This reaction mixture was then added to the solution of ethylchloroformate (10 eq.) in dry THF at −78° C. Reaction mass wan then allowed to come at room temperature and stirred overnight. It was then cooled and quenched with ammonium chloride solution and extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude was then purified using column chromatography to yield 6-tert-butyl 2-ethyl 4,7-dihydrothieno[2,3-c]pyridine-2,6(5H)-dicarboxylate.

Workup

  1. customreaction mixture
  2. customReaction mass wan
  3. customto come at room temperature
  4. stirringstirred overnight
  5. temperatureIt was then cooled
  6. customquenched with ammonium chloride solution
  7. extractionextracted with ethyl acetate
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated
  10. customThe crude was then purified

Sources & evidence

ORD record
ord-4bb23486abc242d4b36a865d2f5d9a90
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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