Lithium hydroxide, monohydrate → HCID 67192009, compound

HRID 546260Notes

Reaction equation

HRID 546260 reaction equation
C[O:2][C:3](=[O:22])[CH:4]([C:11]1[CH:21]=[CH:20][C:14]2[S:15](=[O:19])(=[O:18])[CH2:16][CH2:17][C:13]=2[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.O.[OH-].[Li+]>C(O)C.O>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:21]=[CH:20][C:14]3[S:15](=[O:19])(=[O:18])[CH2:16][CH2:17][C:13]=3[CH:12]=2)[C:3]([OH:22])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67189314HCID 67189314, compound

Product 1

HCID 67192009HCID 67192009, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

3-Cyclopentyl-2-(1,1-dioxo-2,3-dihydro-benzo[b]thiophen-5-yl)-propionic acid methyl ester (184 mg, 0.57 mmol) was dissolved in ethanol (4 mL) and treated with a solution of lithium hydroxide monohydrate (34 mg, 1.43 mmol) in water (1.5 mL) at 25° C. It was stirred at 25° C. until the starting material was all consumed by TLC (˜1 hr). The reaction was then concentrated in vacuo to remove the ethanol. The remaining aqueous layer was then acidified to pH=2 with an aqueous 1N hydrochloric acid solution. This was then extracted with ethyl acetate (3×20 mL), the organic layers combined and dried over magnesium sulfate, filtered and concentrated in vacuo to afford 3-cyclopentyl-2-(1,1-dioxo-2,3-dihydro-benzo[b]thiophen-5-yl)-propionic acid (114 mg, 65%) as a white solid: EI-HRMS m/e calcd for C16H20O4S (M+) 308.1082, observed 308.1075.

Workup

  1. customall consumed by TLC (˜1 hr)
  2. concentrationThe reaction was then concentrated in vacuo
  3. customto remove the ethanol
  4. extractionThis was then extracted with ethyl acetate (3×20 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac80e6736c11471c87e2323bb37af9c3
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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