Thiophene-3-carboxylic acid → HCID 22054376, compound

HRID 1829720Notes

Reaction equation

HRID 1829720 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[CH:2]1.C([N-]C(C)C)(C)C.[Li+].CON(C)[C:20](=[O:24])[CH:21]([CH3:23])[CH3:22]>C1COCC1>[CH3:22][CH:21]([CH3:23])[C:20]([C:2]1[S:1][CH:5]=[CH:4][C:3]=1[C:6]([OH:8])=[O:7])=[O:24]

Participants

5

Reactant 3

HCID 6918Thiophene-3-carboxylic acidHCID 2724682Lithium diisopropylamideHCID 10866371N-Methoxy-N,2-dimethylpropanamide

Product 1

HCID 22054376HCID 22054376, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of thiophene-3-carboxylic acid (26.65 g) in THF (300 ml) was added 2M lithium diisopropylamide (229 ml) dropwise at 0–5° C. with stirring under nitrogen, and the resulting mixture stirred for 15 min. A solution of N-methoxy-N,2-dimethylpropanamide (30 g) in THF (150 ml) was added dropwise over a period of 1 hr. When the addition was complete, the reaction mixture was allowed to warm to room temperature and stirred for 2 hr. It was poured onto water, the layers separated and the aqueous washed with ether. The aqueous was acidified with conc. hydrochloric acid and extracted with ethyl acetate, the organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure to give the sub-title compound as a solid (38.91 g).

Workup

  1. stirringthe resulting mixture stirred for 15 min
  2. additionWhen the addition
  3. stirringstirred for 2 hr
  4. additionIt was poured onto water
  5. customthe layers separated
  6. washthe aqueous washed with ether
  7. extractionextracted with ethyl acetate
  8. dry with materialthe organic extracts were dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ae7a143275614d78b0c537279de6a50e
Source dataset
uspto-grants-2006_06
Patent number
US07064126B2

Reaction notes

Loading…