Methanol → Methyl 3-methylthiophene-2-carboxylate

HRID 1754347Notes

Reaction equation

HRID 1754347 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[CH3:15]O>>[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:15])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 902693-Methyl-2-thenoic acid

Product 1

HCID 580757Methyl 3-methylthiophene-2-carboxylateYield 97%

Procedure

To a solution of 3-Methylthiophene-2-carboxylic acid (15 g, 105 mmol, 1.0 eq) in methanol (150 mL) was added cone sulfuric acid (7.5 mL) drop wise and refluxed for 12 h. The solvent was evaporated under vacuum and the residue was taken into ethyl acetate (200 mL), washed with water (2×50 mL), saturated aqueous sodium bicarbonate solution (2×50 mL), brine (50 mL), dried (Na2SO4) and filtered. The filtrate was evaporated under vacuum to afford 20 g (97%) of the desired product as a oil. 1HNMR (400 MHz, CDCl3) δ 7.38 (d, J=5.0 Hz, 1H), 6.91 (d, J=5.0 Hz, 1H), 3.85 (s, 3H), 2.55 (s, 3H); ESI-MS [(m/z) 157 (MH)+]

Workup

  1. temperaturerefluxed for 12 h
  2. customThe solvent was evaporated under vacuum
  3. washwashed with water (2×50 mL), saturated aqueous sodium bicarbonate solution (2×50 mL), brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-a37b8c5de6274af49b25fb256d1c1b1e
Source dataset
uspto-grants-2015_10
Patent number
US09169242B2

Reaction notes

Loading…