Hydrochloric Acid → HCID 69198691, compound

HRID 2373704Notes

Reaction equation

HRID 2373704 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH2:23][C:24]([O:26]C)=[O:25])=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH3:22])=[CH:15][CH:14]=2)[S:11][CH:12]=1.[OH-].[Na+].Cl>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH2:23][C:24]([OH:26])=[O:25])=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH3:22])=[CH:15][CH:14]=2)[S:11][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86607174HCID 86607174, compound

Product 1

HCID 69198691HCID 69198691, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl [4-(2-chlorophenyl)-2-(4-propoxyphenyl)thien-3-yl]acetate (0.290 g, 0.725 mmol) was dissolved in EtOH (6 mL). NaOH (2.17 mL, 1N, 2.17 mmol) was added and the solution heated to reflux for 5 h. HCl (2.17 mL, 2N, 4.34 mmol) was added and the solvent removed. The mixture was partioned between EtOAc and H2O. The EtOAc layer was dried (MgSO4) and the solvent removed to yield [4-(2-chlorophenyl)-2-(4-propoxyphenyl)thien-3-yl]acetic acid (0.262 g) as a clear oil. 1H NMR (500 MHz, DMSO-d6) δ: 0.95 (t, 3H, J=7.44 Hz), 1.70 (m, 2H), 3.30 (s, 2H), 3.93 (t, 2H, J=6.47 Hz), 6.99 (d, 2H, J=8.78 Hz), 7.28 (dd, 1H, J=1.71 and 7.20 Hz), 7.38 (m, 5H), 7.51 (dd, 1H, J=1.71 and 7.44 Hz), 12.11 (bs, 1H). MS (ES) m/z 387.0 ([M+H]+). MS (ES) m/z 404.1 ([M+NH4]+).

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux for 5 h
  3. customthe solvent removed
  4. dry with materialThe EtOAc layer was dried (MgSO4)
  5. customthe solvent removed

Sources & evidence

ORD record
ord-fae920f1d7a84e9bbee4954abe740204
Source dataset
uspto-grants-2008_12
Patent number
US07459567B2

Reaction notes

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