Water → HCID 68900017, compound

HRID 493102Notes

Reaction equation

HRID 493102 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:23])[C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:7]=1[S:13][C:14]1[C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=2[S:17][CH:18]=1.C1COCC1.O.O>C(OCC)(=O)C>[S:17]1[CH:18]=[C:14]([S:13][C:7]2[CH:8]=[CH:9][C:10]([CH3:12])=[CH:11][C:6]=2[C:5]([OH:23])=[O:4])[C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 21881883Oxolane--water (1/1)HCID 68896559HCID 68896559, compound

Product 1

HCID 68900017HCID 68900017, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

LiOH (480 mg, 20 mmol) is added to 2-(benzo[b]thiophen-3-ylsulfanyl)-5-methyl-benzoic acid methyl ester (630 mg, 2 mmol) in 16 mL mixture of THF/water (3:1). The reaction mixture is refluxed for 2 hours and cooled to room temperature. Water and ethyl acetate is added and the organic phase is washed with brine, dried with MgSO4 and concentrated in vacuo to give the title compound, which is used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture is refluxed for 2 hours
  2. washthe organic phase is washed with brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-220019e714c24c84ae7a6bcc952ac9da
Source dataset
uspto-grants-2009_05
Patent number
US07534791B2

Reaction notes

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