Sodium Hydroxide → 3-(5-Chlorothiophen-2-yl)propanoic acid

HRID 1432884Notes

Reaction equation

HRID 1432884 reaction equation
[OH-:1].[Na+].[Cl:3][C:4]1[S:8][C:7]([CH2:9][CH2:10][CH:11]=[O:12])=[CH:6][CH:5]=1>O.[N+]([O-])([O-])=O.[Ag+]>[Cl:3][C:4]1[S:8][C:7]([CH2:9][CH2:10][C:11]([OH:1])=[O:12])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53788388HCID 53788388, compound

Product 1

HCID 391047953-(5-Chlorothiophen-2-yl)propanoic acid

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Procedure

Silver nitrate (117 mg, 0.69 mmol) in 1 mL of H2O is added to 1.36 mL of 1N NaOH at 0° C. and stirred for 5 minutes. To the brown suspension is added 3-(5-chloro-thiophen-2-yl)-propionaldehyde (60 mg, 0.34 mmol) and the resulting mixture is allowed to warm to room temperature over 2 hours. The precipitate is filtered and washed with hot water (2×). The combined aqueous layers are acidified with 6 N HCl and extracted with EtOAc (2×). The combined organic layers are washed with water (2×), then dried over MgSO4, filtered and concentrated in vacuo to give the title compound (50 mg, 0.26 mmol) as a beige solid. The crude material can be used in the subsequent step without further purification. 1H NMR (CDCl3, 300 MHz) δ6.72 (d, 1H), 6.60 (d, 1H), 3.07 (t, 2H), 2.71 (t, 2H).

Workup

  1. filtrationThe precipitate is filtered
  2. washwashed with hot water (2×)
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic layers are washed with water (2×)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e820a87cc482495399647f7eb908e7c8
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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