Water → HCID 54044087, compound

HRID 863607Notes

Reaction equation

HRID 863607 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:20])=[C:7]([CH3:19])[C:8]2[O:12][C:11]([CH3:14])([CH3:13])[CH:10]([CH2:15]Br)[C:9]=2[C:17]=1[CH3:18])(=[O:3])[CH3:2].[C:21]1(=[O:31])[NH:25][C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12.[K].O>CN(C)C=O>[C:1]([O:4][C:5]1[C:6]([CH3:20])=[C:7]([CH3:19])[C:8]2[O:12][C:11]([CH3:14])([CH3:13])[CH:10]([CH2:15][N:25]3[C:24](=[O:26])[C:23]4=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]4[C:21]3=[O:31])[C:9]=2[C:17]=1[CH3:18])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 19696142HCID 19696142, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 54044087HCID 54044087, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4.75 g of 5-acetoxy-3-bromomethyl-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran (see Example 3) and 2.58 g (1 equivalent)of potassium phthalimide in 50 ml of dry dimethylformamide is stirred at 60° C. for 48 hours. Water is added and the product is extracted twice with ethyl ether. The extract is washed with water and brine, and is dried over anhydrous sodium sulfate. After filtration, evaporation of the solvent leaves a residue that is crystallized from ethyl acetate/heptane. The first crop contains free phthalimide, but subsequent crops yield 2,3-dihydro-2,2,4,6,7-pentamethyl-3-phthalimidomethyl-1-benzofuran-5-ol acetate.

Workup

  1. extractionthe product is extracted twice with ethyl ether
  2. washThe extract is washed with water and brine
  3. dry with materialis dried over anhydrous sodium sulfate
  4. filtrationAfter filtration, evaporation of the solvent
  5. customleaves a residue that
  6. customis crystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-7bcb32f5f0e24557b7475f2d0c51400c
Source dataset
uspto-grants-1998_02
Patent number
US05721233

Reaction notes

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