Lithium hydroxide, monohydrate → HCID 59409753, compound

HRID 1892082Notes

Reaction equation

HRID 1892082 reaction equation
O.[OH-].[Li+].[CH2:4]([C:11]1[CH:12]=[C:13]([C:16]([O:18]CC)=[O:17])[S:14][CH:15]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>O.C1COCC1.CO>[CH2:4]([C:11]1[CH:12]=[C:13]([C:16]([OH:18])=[O:17])[S:14][CH:15]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59409771HCID 59409771, compound

Product 1

HCID 59409753HCID 59409753, compoundYield 98.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide hydrate (1.20 g, 28.3 mmol) in water (50 mL) was added to a solution of compound 1017 (2.4 g, 9.4 mmol) in THF (50 mL) and methanol (30 mL). The reaction mixture was stirred at room temperature for 12 hours. After removal of organic solvent, the aqueous solution was acidified to pH 4.0 with 6 N hydrochloric acid solution and extracted with EtOAc. The organic layer was dried and concentrated to give 4-heptylthiophene-2-carboxylic acid (1018, 2.1 g) which was directly used in the next step without further purification. Rf=0.03 (10% EtOAc in hexane).

Workup

  1. customAfter removal of organic solvent
  2. extractionextracted with EtOAc
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d2055e81aaf04e91adfef20c80d438e7
Source dataset
uspto-grants-2013_08
Patent number
US08507647B2

Reaction notes

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