Hydrochloric Acid → HCID 11316987, compound

HRID 730991Notes

Reaction equation

HRID 730991 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH:12]=[C:11]([C:13]([CH2:31][CH3:32])([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([CH2:28][CH3:29])([OH:27])[CH2:25][CH3:26])=[C:18]([CH3:30])[CH:17]=3)[CH2:14][CH3:15])[S:10][C:9]=2[CH:33]=1)=[O:4].[OH-].[Na+].Cl>CO.O>[CH2:14]([C:13]([C:11]1[S:10][C:9]2[CH:33]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[CH:7][C:8]=2[CH:12]=1)([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([CH2:25][CH3:26])([OH:27])[CH2:28][CH3:29])=[C:18]([CH3:30])[CH:17]=1)[CH2:31][CH3:32])[CH3:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57835397HCID 57835397, compound

Product 1

HCID 11316987HCID 11316987, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

2-{1-Ethyl-1-[4-(2-ethyl-2-hydroxy-butoxy)-3-methyl-phenyl]-propyl}benzo[b]thiophene-6-carboxylic acid methyl ester (0.48 g, 1.02 mmol) is dissolved in MeOH (2 mL) and treated with H2O (0.5 mL) and NaOH (0.20 g, 5.12 mmol). The resulting mixture is heated at a reflux for 2 h, cooled to RT, and stirred overnight. The solution is diluted with H2O (10 mL), adjusted to pH 3-4 using 1 M HCl, and extracted with EtOAc (40 mL). The EtOAc layer is washed with brine (20 mL), dried with MgSO4, filtered, and concentrated to yield the title compound (0.42 g, 0.92 mmol, 89%). 1H NMR (CDCl3), δ 0.76 (t, J=7.5 Hz, 6H), 0.95 (t, J=7.5 Hz, 6H), 1.68 (q, J=14.8, 7.5 Hz, 4H), 2.25-2.27 (m, 7H), 3.82 (s, 2H), 6.74 (d, J=8.8 Hz, 1H), 7.05 (d, J=2.3 Hz, 1H), 7.09 (dd, J=8.5, 2.1 Hz, 1H), 7.24 (s, 1H), 7.75 (d, J=8.4 Hz, 1H), 7.96 (dd, J=8.3, 1.7 Hz, 1H), 8.48 (d, J=1.7 Hz, 1H). Exact mass (m/z): calcd. for C27H35O4S (M+H)+: 454.2; found: 472.3.

Workup

  1. temperatureThe resulting mixture is heated at
  2. temperaturea reflux for 2 h
  3. extractionextracted with EtOAc (40 mL)
  4. washThe EtOAc layer is washed with brine (20 mL)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-724b38016a65435c9f6d8e4bb62dcea3
Source dataset
uspto-grants-2009_09
Patent number
US07582775B2

Reaction notes

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