Sodium Hydroxide → 5-[2-Methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylic acid

HRID 2217097

Reaction equation

HRID 2217097 reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][C:15]([Si:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][C:3]=1[O:4][C:5]1[O:9][C:8]([C:10]([O:12]C)=[O:11])=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O>[CH3:1][C:2]1[CH:17]=[CH:16][C:15]([Si:18]([CH3:19])([CH3:21])[CH3:20])=[CH:14][C:3]=1[O:4][C:5]1[O:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53397016Methyl 5-[2-methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylate2×

Product 1

HCID 692212945-[2-Methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylic acidYield 87.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 5-[2-methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylate (Intermediate 4; 217 mg, 0.71 mmol) in methyl alcohol (3 mL) at room temperature was added a solution of sodium hydroxide (126 mg) in water (1 mL) and the reaction stirred for 18 hours. The resulting mixture was concentrated under reduced pressure, the residue taken up in water and extracted into diethyl ether (1×20 mL). The aqueous layer was acidified with hydrochloric acid (1 M) and extracted with ethyl acetate (2×25 mL). The organic extracts were dried (magnesium sulphate) and concentrated under reduced pressure to give the title compound as a colourless powder (181 mg, 87%). Rf=0.21 (9:1, dichloromethane-methyl alcohol). LCMS Rt=4.33 minutes, m/z=291 (MH+).

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. extractionextracted into diethyl ether (1×20 mL)
  3. extractionextracted with ethyl acetate (2×25 mL)
  4. dry with materialThe organic extracts were dried (magnesium sulphate)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7207bda33a6d4baaae05f653b539a24a
Source dataset
uspto-grants-2008_08
Patent number
US07407649B2

Linked notes

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