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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1508615Generated: October 31, 2026

Ethyl Acetate → HCID 131734114, compound

https://huagongshe.com/reaction/1508615

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantLithium BromideHCID 82050—
ReactantHCID 131734112HCID 131734112—
Solvent1,3-Dimethyl-2-imidazolidinoneHCID 6661—
SolventTetrahydrofuranHCID 8028—
ProductHCID 131734114HCID 13173411492.5%

Reaction Conditions

Temperature65 °C

Reaction Steps

451 mg of lithium bromide was added to a solution of 1.15 g of (2R,3R,4R)-2-fluoro-3,5-bis((4-methoxybenzyl)oxy)-4-(2,4,5-trichlorophenoxy)pentan al O-methyloxime in 6 mL of tetrahydrofuran and 6 mL of 1,3-dimethyl-2-imidazolidinone, and the obtained mixture was then stirred at 65° C. for 7 hours. Thereafter, ethyl acetate and a 25% lithium bromide aqueous solution were added to the reaction mixture. The organic layer was fractionated, and it was washed with a 12% lithium bromide aqueous solution and was then dried over anhydrous sodium sulfate. After that, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 to 60/40), so as to obtain 857 mg of (2S,3S,4S)-4-bromo-2-fluoro-3,5-bis((4-methoxybenzyl)oxy)pentanal O-methyloxime in the form of a colorless oily product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09221865B2
Source datasetuspto-grants-2015_12
ORD IDord-f956ce63628842ab9b970efdbccbdbb0
Source noteuspto-grants-2015_12