Hydrochloric Acid → HCID 11417526, compound

HRID 1359535Notes

Reaction equation

HRID 1359535 reaction equation
C(OC[S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:18][S:17][C:16]=2[C:26]([O:28][CH3:29])=[O:27])=[CH:11][C:10]=1[F:30])(=[O:8])=[O:7])(=O)C.C[O-].[Na+].C(OCC)(=O)C.Cl>O1CCCC1.CO>[F:30][C:10]1[CH:11]=[C:12]([C:15]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:18][S:17][C:16]=2[C:26]([O:28][CH3:29])=[O:27])[CH:13]=[CH:14][C:9]=1[S:6]([OH:8])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 18183323HCID 18183323, compound

Product 1

HCID 11417526HCID 11417526, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The methyl 3-[4-[[(acetyloxy)methyl]sulfonyl]3-fluorophenyl]-4-phenyl-2-thiophenecarboxylate (2.75 g, 6.13 mmol) was dissolved in tetrahydrofuran (100 mL) and stirred at room temperature. 25% Sodium methoxide in methanol (3.0 mL) was added and the solution stirred for 5 min. The resulting slurry was poured into ethyl acetate (200 mL) and aqueous 1N hydrochloric acid (100 mL) was added. The solution was stirred and the layers allowed to separate. The organic layer was collected and the aqueous layer back extracted with ethyl acetate (100 mL). The organic layers were combined, extracted with brine, dried over sodium sulfate, and solvent removed at reduced pressure. The 2-methyl 3-(3-fluoro-4-sulfinophenyl)-4-phenyl-2-thiophenecarboxylate (1.87 g, 4.59 mmol) was isolated as a white solid.(77% yield). Mp 132.6-133.1° C. 1H NMR (CDCl3/300 MHz) 7.74-7.80 (1H, m), 7.55 (s, 1H), 6.80-7.28 (m, 6H), 3.74 (s, 3H). ESHRMS m/z 394.0586 (calcd for M+NH4+, 394.0583).

Workup

  1. stirringthe solution stirred for 5 min
  2. additionwas added
  3. stirringThe solution was stirred
  4. customto separate
  5. customThe organic layer was collected
  6. extractionthe aqueous layer back extracted with ethyl acetate (100 mL)
  7. extractionextracted with brine
  8. dry with materialdried over sodium sulfate, and solvent
  9. customremoved at reduced pressure

Sources & evidence

ORD record
ord-039b09529ac94962a42dc47925855bcb
Source dataset
uspto-grants-2003_07
Patent number
US06600052B1

Reaction notes

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