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- W2103242623 abstract "[136453-62-8] C21H27ClO2Si2 (MW 403.06)InChI = 1S/C21H27ClO2Si2/c1-25(2,3)14-7-9-16-17-10-8-15(26(4,5)6)12-19(17)20(18(16)11-14)13-24-21(22)23/h7-12,20H,13H2,1-6H3InChIKey = OQYBDUDMTQOYAI-UHFFFAOYSA-N(reagent for the introduction of a more soluble Fmoc protecting group for amines and alcohols)Alternate Name: 2,7-bis(trimethylsilyl)fluorenylmethoxycarbonyl chloride; Bts-Fmoc-Cl.Physical Data: mp 64–66 °C, colorless crystals.1Solubility: soluble in CH2Cl2, CHCl3, and THF.Analysis of Reagent Purity: 1H NMR, IR, elemental analysis.1Preparative Methods: the title compound 1 is obtained by the action of phosgene on 2,7-bis(trimethylsilyl)-9-fluorenylmethanol 6. This alcohol can be obtained from 9,9-bis(trimethylsilyl)fluorene 22 which, on treatment with NBS/HBr, is converted to the corresponding 2,7-dibromo compound 3. Silylation with Me3SiCl followed by selective protodesilylation at the 9-position effected by KOH/EtOH, leads to the 2,7-bis(trimethylsilyl)fluorene 5. Reaction of 5 with n-BuLi and formaldehyde then generates the required alcohol (eq 1).1(1)Purification: recrystallization from Skelly F (saturated hydrocarbon solvent, bp range 30–60 °C).1Handling, Storage, and Precautions: moisture sensitive; protect from heat. Prolonged storage of the reagent can lead to extrusion of CO2, causing pressure to develop inside the bottle. Converted to the Fmoc function itself upon treatment with trifluoroacetic acid. Probably toxic. Use in a well-ventilated fumehood." @default.
- W2103242623 created "2016-06-24" @default.
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- W2103242623 date "2003-10-15" @default.
- W2103242623 modified "2023-09-26" @default.
- W2103242623 title "2,7-Bis(trimethylsilyl)fluorenylmethyl Chloroformate" @default.
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- W2103242623 doi "https://doi.org/10.1002/047084289x.rn00301" @default.
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