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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1404960Generated: November 1, 2026

Diethyl Ether → HCID 67959083, compound

https://huagongshe.com/reaction/1404960

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantCyclobutanoneHCID 14496—
ReactantHCID 67959348HCID 67959348—
ReactantButyllithiumHCID 178418339—
SolventWaterHCID 962—
SolventHexaneHCID 8058—
ProductHCID 67959083HCID 6795908358.5%

Reaction Conditions

Temperature-78 °C

Reaction Steps

To a solution of tert-butyl 8-bromo-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate (334 mg) obtained in Example 1, steps 1-3, and Et2O (10 mL) was added dropwise 1.6 N hexane solution of n-butyllithium (72.4 ml) at −78° C., and the mixture was stirred at −78° C. for 15 min. Cyclobutanone (0.0747 ml) was added, and the mixture was stirred at −78° C. for 1 hr. To the reaction mixture was added water (10 mL), and the organic layer was separated and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (solvent gradient; 0→50% ethyl acetate/hexane) to give the title compound (190 mg, 58.5%) as an oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08916549B2
Source datasetuspto-grants-2014_12
ORD IDord-c17957dc14ba45e7a39d29fb35a93c9c
Source noteuspto-grants-2014_12