Sulfuric Acid → Ethyl 3-(6-{2-[6-(methylamino)-2-pyridyl]ethoxy}benzo[b]furan-3-yl)propanoate

HRID 985498Notes

Reaction equation

HRID 985498 reaction equation
S(=O)(=O)(O)O.[CH3:6][NH:7][C:8]1[N:13]=[C:12]([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[C:19]([CH:31]=[CH:32][CH:33]=2)[O:20][CH2:21][C:22](=O)[CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:11]=[CH:10][CH:9]=1.C(=O)([O-])O.[Na+]>>[CH3:6][NH:7][C:8]1[N:13]=[C:12]([CH2:14][CH2:15][O:16][C:17]2[CH:33]=[CH:32][C:31]3[C:22]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][O:20][C:19]=3[CH:18]=2)[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 11749501Ethyl 5-(3-{2-[6-(methylamino)(2-pyridyl)]ethoxy}phenoxy)-4-oxopentanoate

Product 1

HCID 11326106Ethyl 3-(6-{2-[6-(methylamino)-2-pyridyl]ethoxy}benzo[b]furan-3-yl)propanoateYield 57%

Procedure

Concentrated sulfuric acid (3ml) was cooled in an ice-water bath to 0° C. and added to a flask containing ethyl 5-(3-{2-[6-(methylamino)(2-pyridyl)]ethoxy}phenoxy)-4-oxopentanoate (190 mg, 0.5 mmol) at 0° C. The reaction was stirred 15 minutes and then poured over ice. The solution was neutralized with solid sodium hydrogencarbonate (pH=7) and the product was extracted with ethyl acetate. The organic layer was dried, filtered and evaporated under vacuum to yield 104 mg (57%) of Ethyl 3-(6-{2-[6-(methylamino)-2-pyridyl]ethoxy}benzo[b]furan-3-yl)propanoate. NMR 1H Cl3CD δ: 7.36 (m, 3H), 7.01 (d, 1H, J=2.1 Hz), 6.87 (dd, 1H, J=8.5, 2.1 Hz), 6.54 (d, 1H, J=7.2 Hz), 6.23 (d, 1H, J=8.2 Hz), 4.68 (br s, 1H), 4.15 (c, 2H, J=7.4 Hz), 3.09 (t, 2H, J=6.9 Hz), 2.97 (t, 2H, J=6.9 Hz), 2.87 (d, 3H, J=5.1 Hz), 2.68 (t, 2H, J=6.9 Hz), 1.26 (t, 1H, J=7.4 Hz).

Workup

  1. additionadded to a flask
  2. additionpoured over ice
  3. extractionthe product was extracted with ethyl acetate
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-2b3cc6a7b38d4841845e244b70ef75b4
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

Loading…