Chloromethyl Methyl Ether → Methyl 3'-methoxymethoxymethylbiphenyl-4-carboxylate

Temperature

0 °C

Chloromethylmethyl ether (0.24 ml) and diisopropylethylamine (0.74 ml) was added to a solution of methyl 3′-hydroxymethylbiphenyl-4-carboxylate (504 mg), which is the product of Reference example 15(a), in anhydrous dichloromethane (10 ml) at 0° C. The mixture was stirred at 0° C. for 1 hour and then allowed to stand at ambient temperature for 14 hours. The reaction mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water and the layers were separated. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified via chromatography on a silica gel column using hexane/ethyl acetate=2/1 as the eluant to afford the desired compound (467 mg) as colorless crystals.

1. customat 0° C
2. waitto stand at ambient temperature for 14 hours
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. customThe residue was partitioned between ethyl acetate and water
5. customthe layers were separated
6. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified via chromatography on a silica gel column

ORD record

ord-f766b61d00154f5da66790c7f51c4f17

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06528525B1