Lithium Hydroxide → [4-(4,9-diethoxy-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetic Acid

HRID 1375141Notes

Reaction equation

HRID 1375141 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:20][C:19]3[C:18]([O:21][CH2:22][CH3:23])=[C:17]4[CH:24]=[CH:25][CH:26]=[CH:27][C:16]4=[C:15]([O:28][CH2:29][CH3:30])[C:14]=3[CH2:13]2)=[CH:8][CH:7]=1)C.[OH-].[Li+]>O1CCCC1.O>[CH2:22]([O:21][C:18]1[C:19]2[CH2:20][N:12]([C:9]3[CH:8]=[CH:7][C:6]([CH2:5][C:4]([OH:31])=[O:3])=[CH:11][CH:10]=3)[CH2:13][C:14]=2[C:15]([O:28][CH2:29][CH3:30])=[C:16]2[CH:27]=[CH:26][CH:25]=[CH:24][C:17]=12)[CH3:23]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 131726211ethyl[4-(4,9-diethoxy-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate

Product 1

HCID 21079276[4-(4,9-diethoxy-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetic AcidYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl[4-(4,9-diethoxy-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate (10 mg, 0.024 mmol) in tetrahydrofuran (4 ml) and a solution of lithium hydroxide (6 mg, 0.24 mmol) in water (1 ml) were stirred vigorously for 14 h. The reaction mixture was diluted with water (10 ml) and extracted with ethyl acetate (2×5 ml) and the organic extracts discarded. The aqueous phase was acidified with 2N hydrochloric acid to pH=5 and extracted with ethyl acetate (3×5 ml). The combined organic extracts were dried over magnesium sulphate and the solvent removed in vacuo to give the product as a red solid (4 mg, 43%).

Workup

  1. extractionextracted with ethyl acetate (2×5 ml)
  2. extractionextracted with ethyl acetate (3×5 ml)
  3. dry with materialThe combined organic extracts were dried over magnesium sulphate
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ab0fbc7b27d84ec8a64ed67f08760450
Source dataset
uspto-grants-2007_01
Patent number
US07166631B2

Reaction notes

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