Abstract
[22101-66-2] C9H9FO (MW 152.17) InChI = 1S/C9H9FO/c10-9(8-6-11-8)7-4-2-1-3-5-7/h1-5,8-9H,6H2/t8-,9+/m0/s1 InChIKey = KDCLZRHLDRBQFC-DTWKUNHWSA-N (a chiral derivatizing agent for amines1) Physical Data: colorless liquid. Solubility: miscible with hydrocarbon solvents (hexane, toluene), ethers (diethyl ether, THF, 1,2-dimethoxyethane, 1,4-dioxane, diglyme), and halogenated solvents (dichloromethane, chloroform, 1,2-dichloroethane). Form Supplied in: not commercially available. Analysis of Reagent Purity: NMR. Preparative Method: from (2S,3S)-3-phenylglycidyl tosylate,2 via ring-opening hydrofluorination3 and epoxide formation with lithium tert-butoxide in THF. Purification: the product is obtained essentially pure. Trace impurities are removed by column chromatography on silicagel, eluting with hexane/ethyl acetate mixtures. Handling, Storage, and Precautions: epoxides are known alkylating agents that should be handled with care. The reagent can be stored at 6 °C for weeks without any alteration. (2S,3S)-3-Phenylglycidyl tosylate, a solid and very stable material, is a convenient relay for the reagent. Contact with nucleophilic reagents that can potentially perform epoxide ring-opening should be avoided.
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