Sodium Hydroxide → HCID 86713222, compound

HRID 1056823Notes

Reaction equation

HRID 1056823 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([O:12][CH3:13])[CH:5]=1.[C:14]([O:17][C@@H:18]1[C@@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:22]([O:28][C:29](=[O:31])[CH3:30])[C@@H:21]([CH2:32][O:33][C:34](=[O:36])[CH3:35])[O:20][C@@H:19]1Br)(=[O:16])[CH3:15]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)(Cl)Cl>[CH3:13][O:12][C:6]1[CH:5]=[C:4]([O:3][C@@H:19]2[O:20][C@H:21]([CH2:32][O:33][C:34](=[O:36])[CH3:35])[C@@H:22]([O:28][C:29](=[O:31])[CH3:30])[C@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:18]2[O:17][C:14](=[O:16])[CH3:15])[CH:11]=[CH:10][C:7]=1[CH:8]=[O:9]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 5195414-Hydroxy-2-Methoxybenzaldehyde

Product 1

HCID 86713222HCID 86713222, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6212ChloroformSolvent

Procedure

A 1N sodium hydroxide aqueous solution (10.4 mL) was added to a solution of 666 mg (4.38 mmol) of 4-hydroxy-2-methoxybenzaldehyde, 1.50 g (3.65 mmol) of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide, and 1.18 g (3.66 mmol) of tetrabutylammonium bromide in chloroform (11 mL) at room temperature, and the mixture was vigorously stirred for 1 hour. The reaction mixture was subjected to extraction with ethyl acetate. After washing with a saturated sodium bicarbonate solution and then with saturated brine, drying over magnesium sulfate was performed. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=75/25 to 60/40) to give 606 mg (40% yield) of 2-methoxy-4-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) oxy]benzaldehyde as a white powder.

Workup

  1. extractionThe reaction mixture was subjected to extraction with ethyl acetate
  2. washAfter washing with a saturated sodium bicarbonate solution
  3. dry with materialwith saturated brine, drying over magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=75/25 to 60/40)

Sources & evidence

ORD record
ord-c36ab5772ba8426ca80bf1960ec77996
Source dataset
uspto-grants-2016_07
Patent number
US09399635B2

Reaction notes

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