Tetrahydrofuran → (1-Benzenesulfonyl-1H-pyrrol-3-yl)-acetic acid

HRID 2249512Notes

Reaction equation

HRID 2249512 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:9]=[CH:8][N:7]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:6]=1.C1COCC1.O[Li].O>O>[C:13]1([S:10]([N:7]2[CH:8]=[CH:9][C:5]([CH2:4][C:3]([OH:19])=[O:2])=[CH:6]2)(=[O:12])=[O:11])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 5557741-(Phenylsulfonyl)-3-(carbomethoxymethyl)pyrrole

Product 1

HCID 13157056(1-Benzenesulfonyl-1H-pyrrol-3-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of (1-benzenesulfonyl-1H-pyrrol-3-yl)-acetic acid methyl ester (1.4 g, 5.01 mmol) in co-solvents of THF and water (1:1, 10 mL) was added LiOH hydrate (0.84 g, 20 mmol). The mixture was stirred at room temperature for 45 minutes and diluted with 50 mL of water. The resulting aqueous solution was washed once with EtOAc, acidified with 6N HCl, and extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated to a sticky yellow oil (1.33 g, 100%). The crude product was used directly. MS (ES+): m/e=266.1 (M+H); LC/Method A/3.08 min.

Workup

  1. washThe resulting aqueous solution was washed once with EtOAc
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated to a sticky yellow oil (1.33 g, 100%)
  5. customLC/Method A/3.08 min.

Sources & evidence

ORD record
ord-03487360535348ab88c7e617189a0fa1
Source dataset
uspto-grants-2008_01
Patent number
US07314885B2

Reaction notes

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