Dimethylformamide → HCID 19757261, compound

HRID 1588144Notes

Reaction equation

HRID 1588144 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][O:11][CH3:12])[C:6]([O:13][CH3:14])=[C:5]([OH:15])[C:4]=1[O:16][CH2:17][O:18][CH3:19].[H-].[Na+].[I:22][CH2:23][CH2:24][CH2:25]I.[C:27](OCC)(=[O:29])C.CN(C)[CH:35]=[O:36]>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]([O:29][CH3:27])[O:11][CH3:12])[C:6]([O:13][CH3:14])=[C:5]([O:15][CH2:25][CH2:24][CH2:23][I:22])[C:4]=1[O:16][CH:17]([O:36][CH3:35])[O:18][CH3:19]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 123141,3-DiiodopropaneHCID 24758Sodium hydrideHCID 19757160HCID 19757160, compound

Product 1

HCID 19757261HCID 19757261, compound

Procedure

521 Milligrams of 1,4-dimethoxy-2,5-bis(methoxymethyoxy)-3-hydroxybenzene was dissolved in 8 ml of dimethylformamide, under an ice-cooling condition, 40 mg of sodium hydride (60% dispersion in oil) was added thereto, and 1 milliliter of 1,3-diiodopropane was further added to the reaction mixture and stirred at room temperature for 14 hours. 50 Milliliters of ethyl acetate was added to the reaction mixture and washed with water, a saturated sodium chloride aqueous solution and dried, then purified by means of a silica gel column chromatography (diameter 2 cm×length 10 cm, adsorbent: "Silica gel" manufactured by E. Merck A. G., developing solvent: 20% ethyl acetate-n-hexane) to obtain 318 mg of 1,4-dimethoxy-2,5-bis(dimethoxymethoxy)-3-(3-iodopropoxy)benzene. Colorless oily substance.

Workup

  1. additionwas added
  2. washwashed with water
  3. dry with materiala saturated sodium chloride aqueous solution and dried
  4. custompurified by means of a silica gel column chromatography (diameter 2 cm×length 10 cm, adsorbent: "Silica gel" manufactured by E. Merck A. G., developing solvent: 20% ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-6b309e4805d3489288f9c4456dde4648
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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