Hydrochloric Acid → Methyl 6-hydroxybenzofuran-3-carboxylate

HRID 1947491Notes

Reaction equation

HRID 1947491 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][Si](C(C)(C)C)(C)C)=[CH:13][C:8]=2[O:7][CH:6]=1)=[O:4].Cl>CO>[CH3:1][O:2][C:3]([C:5]1[C:9]2[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[O:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 595775816-(Tert-butyl-dimethyl-silanyloxy)-benzofuran-3-carboxylic acid methyl ester

Product 1

HCID 59577559Methyl 6-hydroxybenzofuran-3-carboxylateYield 94.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 6-(tert-butyl-dimethyl-silanyloxy)-benzofuran-3-carboxylic acid methyl ester (2.4 g, 7.7 mmol) was added 1% HCl in MeOH (70 mL) and the resulting solution was stirred (rt, 14 h). The reaction mixture was concentrated in vacuo. The resulting solid was dissolved in DCM (100 mL) and sat. NaHCO3 (50 mL) was added. A solid formed and was filtered to afford the title compound as a white solid (1.4 g, 94%). MS (ESI): mass calcd. for C10H8O4, 192.04; m/z found, 193.1 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.24 (s, 1H), 7.77 (d, J=8.5, 1H), 6.94 (d, J=1.4, 1H), 6.86 (dd, J=8.5, 1.7, 1H), 3.90 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe resulting solid was dissolved in DCM (100 mL)
  3. additionsat. NaHCO3 (50 mL) was added
  4. customA solid formed
  5. filtrationwas filtered

Sources & evidence

ORD record
ord-e790b8d9d94d4126a8dd8b982e1e83b7
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

Loading…