Dimethylformamide → HCID 22502881, compound

HRID 1006930Notes

Reaction equation

HRID 1006930 reaction equation
[H-].[Na+].CN(C)C=O.[I:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.[O:16]1[CH2:20][CH2:19][O:18][CH:17]1[CH2:21]Br>O>[O:16]1[CH2:20][CH2:19][O:18][CH:17]1[CH2:21][O:15][C:12]1[CH:13]=[CH:14][C:9]([I:8])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 108944-IodophenolHCID 24758Sodium hydrideHCID 780681,3-Dioxolane, 2-(bromomethyl)-

Product 1

HCID 22502881HCID 22502881, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 65% sodium hydride (9.3 g)/dimethylformamide (100 ml) was ice-cooled, followed by the addition of 4-iodophenol (50.5 g)/dimethylformamide (200 ml) solution, and the mixture was stirred for 3 hr. To the mixture solution was added (1,3-dioxolan-2-yl)methylbromide (46.0 g), and the mixture was reacted at 60° C. for 1 day. The reaction solution was poured into water, and extracted with ethyl acetate. The resulting organic layer was washed with water and brine, and then dried (over magnesium sulfate). The solvent was removed, and the resulting residue was purified by NH silica gel column chromatography (chloroform), and then recrystallized from ethyl acetate/hexane, to give 32.7 g of the title compound as pale yellow prisms.

Workup

  1. temperaturecooled
  2. customthe mixture was reacted at 60° C. for 1 day
  3. extractionextracted with ethyl acetate
  4. washThe resulting organic layer was washed with water and brine
  5. dry with materialdried (over magnesium sulfate)
  6. customThe solvent was removed
  7. customthe resulting residue was purified by NH silica gel column chromatography (chloroform)
  8. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-70acb2b0de6d4e558563fab53a329790
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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