Tetrahydrofuran → HCID 66895113, compound

HRID 19319Notes

Reaction equation

HRID 19319 reaction equation
C[O:2][C:3](=[O:25])[CH:4]([N:11]1[CH2:15][C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[CH:13][C:12]1=[O:24])[CH2:5][CH2:6][C:7]([F:10])([F:9])[F:8].O1CCCC1.O.[OH-].[Li+]>O>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[O:16][C:14]1[CH2:15][N:11]([CH:4]([CH2:5][CH2:6][C:7]([F:10])([F:9])[F:8])[C:3]([OH:25])=[O:2])[C:12](=[O:24])[CH:13]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 66895286HCID 66895286, compound

Product 1

HCID 66895113HCID 66895113, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-5,5,5-trifluoro-pentanoic acid methyl ester (1.02 g, 2.70 mmol) in a 1:1 solution of tetrahydrofuran:water (30 mL) was treated with lithium hydroxide monohydrate (270 mg, 5.40 mmol). The mixture was stirred for 2 h at 25° C. After such time, the mixture was concentrated in vacuo to remove the tetrahydrofuran, diluted with water and the pH adjusted to pH=5 with 1N aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-5,5,5-trifluoro-pentanoic acid (766 mg, 78%) as a cream colored solid: HR-ES-MS m/z calculated for C15H13NO4ClF3 [M+H]+ 364.0558, observed 364.0557.

Workup

  1. concentrationAfter such time, the mixture was concentrated in vacuo
  2. customto remove the tetrahydrofuran
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a39ce1e39134b47bc007361ae70fb7b
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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