Sodium Hydroxide → HCID 18472317, compound

HRID 1277268Notes

Reaction equation

HRID 1277268 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:7]2[CH:8]=[CH:9][C:10]3[O:16][CH2:15][CH2:14][C:13]([C:17]([O:19]C)=[O:18])=[CH:12][C:11]=3[CH:21]=2)[S:5][CH:6]=1.[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([C:7]2[CH:8]=[CH:9][C:10]3[O:16][CH2:15][CH2:14][C:13]([C:17]([OH:19])=[O:18])=[CH:12][C:11]=3[CH:21]=2)[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18472481HCID 18472481, compound

Product 1

HCID 18472317HCID 18472317, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (10 ml) was dissolved methyl 7-(4-methyl-2-thienyl)-2,3-dihydro-1-benzoxepine-4-carboxylate (420 mg), and to the mixture was added 1N sodium hydroxide (8.4 ml). The mixture was stirred at room temperature for 15 hours. Under reduced pressure, the organic solvent was removed, and to the residue was added ethyl acetate. The mixture was extracted with water, and to the aqueous layer was added 6N hydrochloric acid to make the solution pH 4-5, which was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was removed to give 7-(4-methyl-2-thienyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid (320 mg).

Workup

  1. customUnder reduced pressure, the organic solvent was removed
  2. additionto the residue was added ethyl acetate
  3. extractionThe mixture was extracted with water
  4. additionto the aqueous layer was added 6N hydrochloric acid
  5. extractionwas extracted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried with magnesium sulfate
  8. customUnder reduced pressure, the solvent was removed

Sources & evidence

ORD record
ord-eae7275b52cd4c3e88217d834c664693
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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