Benzyl Bromide → HCID 86623497, compound

Participants

Reaction Steps

The 6-difluoromethyl-3-hydroxy-2-(1-hydroxy-ethyl)-1-methyl-1H-pyridin-4-one product obtained in the 2 experiments in step 1 above were combined together and dissolved in MeOH (50 mL). A 6.0 M NaOH solution (4 mL, 24 mmol) and BnBr (2.85 mL, 24 mL) were successively added at room temperature. The progress of the reaction was monitored by HPLC Method 1 as described above. After 1.5 hrs, HPLC analysis of the reaction mixture indicated presence of about 15% of unreacted starting material. Thus, another 1 mL of a 6.0 M NaOH solution and 1 mL of BnBr were added, and the mixture was refluxed for 1 hr. The mixture was cooled to room temperature, and evaporated to dryness. The residue was taken up in CH2Cl2, and the organic layer was washed with brine (40 mL). The aqueous brine layer was back washed with CH2Cl2 (40 mL). The organic fractions were combined, dried over Na2SO4, filtered, and evaporated to dryness. The residue was purified by column chromatography on silica gel using a mixture of CH2Cl2 and MeOH (100/3, v/v) as eluant. Fractions rich in product were combined together, and concentrated to give 3-benzyloxy-6-difluoromethyl-2-(1-hydroxy-ethyl)-pyran-4-one (4.00 g) as a bright yellow oil. HPLC purity (peak area percent) of this material is 88.8% at λ=280 nm using HPLC Method 1 as described above.

Provenance & Evidence