Sodium hydride → HCID 84038604, compound

HRID 469164Notes

Reaction equation

HRID 469164 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[OH:9][C:10]1[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=[O:13].[Cl-].[NH4+]>>[O:9]1[C:10]2[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]([OH:13])[CH2:2]1

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 905792,3-Dihydroxybenzaldehyde

Product 1

HCID 84038604HCID 84038604, compoundYield 38.1%

Procedure

To a solution of trimethylsulfoxonium iodide (16.7 g) in dimethylsufoxide (75 ml), sodium hydride (3.19 g) was added, and the resultant mixture was stirred for 1 hour. A solution of 2,3-dihydroxybenzaldehyde (10 g) in dimethylsufoxide (75 ml) was added thereto and the resultant mixture was stirred for 2 days. To the resultant reaction solution, saturated ammonium chloride aqueous solution was added, and extracted with ethyl acetate. The resultant organic phase was washed with a saturated saline, dried over anhydrous sodium sulfate, and filtered. From the reaction mixture, the solvent was distilled off under reduced pressure, followed by purifying the resultant residue by silica gel column chromatography (eluate; n-hexane:ethyl acetate=100:0 to 80:20), and from the resultant, the solvent was distilled off under reduced pressure to obtain the subject compound (4.2 g) as yellow solid.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe resultant organic phase was washed with a saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationFrom the reaction mixture, the solvent was distilled off under reduced pressure
  7. customby purifying the resultant residue by silica gel column chromatography (eluate; n-hexane:ethyl acetate=100:0 to 80:20)
  8. distillationfrom the resultant, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-08480c7d4e5c4009adb280ebdfc4180f
Source dataset
uspto-grants-2014_01
Patent number
US08629102B2

Reaction notes

Loading…