Benzyl Bromide → HCID 10877938, compound

428 mg of sodium hydride (60% in oil) was suspended in 8 ml of THF, and a THF solution (5 ml) of 970 mg of (2R,3S)-1,2-epoxypent-4-ene-3-ol was dropwise added thereto under an argon atmosphere at -10° C. The mixture was stirred at room temperature for 20 minutes. Then, 360 mg of tetra-n-butylammonium iodide and 1.27 ml of benzyl bromide were added thereto at -10° C. The mixture was stirred at room temperature for two hours, and then poured into a saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=0/1) to obtain 1.7 g of (2R,3S)-3-benzyloxy-1,2-epoxy-4-pentene as colorless oily substance.

1. customat -10° C
2. customat -10° C
3. stirringThe mixture was stirred at room temperature for two hours
4. extractionextracted with ethyl acetate
5. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
6. distillationthe solvent was distilled off
7. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=0/1)

ORD record

ord-2d6092f71f274112992cd25250da03d2

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05506356