4-hydroxy-2-methoxybenzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-hydroxy-2-methoxybenzaldehyde (5.23 g; 34.4 mmol), t-butyl bromoacetate (4.9 mL; 30.3 mmol) and K2CO3 (15.1 g; 108.9 mmol) in 50 mL of DMF was stirred at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate, filtered, and partitioned between ethyl acetate and 1 N HCl. The organic phase was washed (sat. NaCl) and dried (MgSO4), and concentrated to give 17.59 g of t-butyl 4-formyl-3-methoxyphenoxyacetate as a white solid. filtered partitioned between ethyl acetate and 1 N HCl The organic phase was washed (sat. NaCl) dried (MgSO4) concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. The reaction mixture was subjected to extraction with ethyl acetate After washing with a saturated sodium bicarbonate solution with saturated brine, drying over magnesium sulfate 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)