Sodium Hydroxide → HCID 53252468, compound

HRID 536612Notes

Reaction equation

HRID 536612 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)=[C:10]([CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])[S:11][CH:12]=2)=[C:4]([O:27][CH3:28])[CH:3]=1.[OH-].[Na+]>CCO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)=[C:10]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[S:11][CH:12]=2)=[C:4]([O:27][CH3:28])[CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67254892HCID 67254892, compound

Product 1

HCID 53252468HCID 53252468, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 3-(4-(4-chloro-2-methoxyphenyl)-3-(4-hydroxyphenyl)thiophen-2-yl)propanoate (220 mg, 0.53 mmol) in EtOH (5 mL) was added NaOH (42 mg, 1.06 mmol), and the mixture was stirred at room temperature for 2 hours. The mixture was diluted with water, neutralized to pH=4-5, extracted with EtOAc, and concentrated to give 3-(4-(4-chloro-2-methoxyphenyl)-3-(4-hydroxyphenyl)thiophen-2-yl)propanoic acid (Scheme II, 12, X1=4-hydroxyphenyl, X2=4-chloro-2-methoxyphenyl) (127.42 mg, yield 62%). 1H NMR (DMSO-d6 400 MHz): δ 9.36 (br, 1H), 7.25 (s, 1H), 7.01 (d, J 8.0 Hz, 1H), 6.91-6.88 (m, 2H), 6.79 (d, J=8.4 Hz, 2H), 6.64 (d, J=8.4 Hz, 2H), 3.40 (s, 3H), 2.92 (t, J=7.2 Hz, 2H), 2.47 (t, J=7.2 Hz, 2H); MS (ESI): m/z [M+1]+=389.0.

Workup

  1. extractionextracted with EtOAc
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e6a4151324f24d00b0a50870b442708d
Source dataset
uspto-grants-2014_10
Patent number
US08859611B2

Reaction notes

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