Water → 6-Methoxy-2-(4-methoxybenzyl)-2,3-dihydroisoindol-1-one

HRID 1761020Notes

Reaction equation

HRID 1761020 reaction equation
C1(P(C2C=CC=CC=2)([CH:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=3)[C:11](=[O:20])[N:10]2[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=O)C=CC=CC=1.[OH-].[Na+].O>C1COCC1>[CH3:19][O:18][C:14]1[CH:13]=[C:12]2[C:17]([CH2:9][N:10]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)[C:11]2=[O:20])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 225942173-(Diphenyl-phosphinoyl)-6-methoxy-2-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one

Product 1

HCID 114375476-Methoxy-2-(4-methoxybenzyl)-2,3-dihydroisoindol-1-oneYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(diphenyl-phosphinoyl)-6-methoxy-2-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one (1.49 g, 3.1 mmol) in THF (40 mL) containing a solution of sodium hydroxide (2.5 M, 12.4 mL, 30.8 mmol) was heated under reflux for 14 h. The solution was then cooled to RT and water (40 mL) added. The mixture was extracted with diethyl ether and the combined organic extracts washed with water and brine. The organic layer was then dried over sodium sulphate, filtered and evaporated. The residue was then purified by chromatography (SiO2, Hexane:Acetone 6:4) to afford the title product (661 mg, 76%) as a light yellow solid. MS m/e=283.2 (M).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 14 h
  3. extractionThe mixture was extracted with diethyl ether
  4. washthe combined organic extracts washed with water and brine
  5. dry with materialThe organic layer was then dried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was then purified by chromatography (SiO2, Hexane:Acetone 6:4)

Sources & evidence

ORD record
ord-cca6b47dfc2346e79177e0aa12b12ba2
Source dataset
uspto-grants-2005_01
Patent number
US06846832B2

Reaction notes

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