Sodium Hydroxide → HCID 7130760, compound

HRID 1892085Notes

Reaction equation

HRID 1892085 reaction equation
[OH-].[Na+].[C:3]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([C:14]([O:16]C)=[O:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1>O.C1COCC1.CO>[C:3]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 12317965Methyl 5-[1,1′-biphenyl]-4-yl-2-thiophenecarboxylate

Product 1

HCID 7130760HCID 7130760, compoundYield 80.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium hydroxide in water (2N, 50 mL) was added to a suspension of compound 1022 (3.5 g, 11.9 mmol) in THF (50 mL) and methanol (50 mL). The reaction mixture was stirred at room temperature for 14 hours and then concentrated to approximately 1/10 of its original volume (15 mL). The concentrated solution was adjusted to pH 2-3 using 2N aqueous hydrochloric acid solution and extracted with a mixture of DCM and ethanol (7:3 ratio, 200 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to give the compound 1023 (2.7 g). 1H NMR (CDCl3, 300 MHz) δ 7.39-7.41 (d, 1H), 7.46-7.51 (m, 2H), 7.63-7.64 (d, 1H), 7.71-7.85 (m, 7H).

Workup

  1. concentrationconcentrated to approximately 1/10 of its original volume (15 mL)
  2. extractionextracted with a mixture of DCM and ethanol (7:3 ratio, 200 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-52516047c3af431aa501bf349d058796
Source dataset
uspto-grants-2013_08
Patent number
US08507647B2

Reaction notes

Loading…