Acetic acid, diazo-, 2-propenyl ester synthesis
- Product Name:Acetic acid, diazo-, 2-propenyl ester
- CAS Number:4606-10-4
- Molecular formula:C5H6N2O2
- Molecular Weight:126.1133
591-87-7
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Yield:4606-10-4 65%
Reaction Conditions:
Stage #1: Allyl acetatewith lithium hexamethyldisilazane in tetrahydrofuran;hexane at -78; for 0.5 h;Inert atmosphere;
Stage #2: with 2,2,2-trifluoroethyl trifluoroacetate in tetrahydrofuran;hexane at -78; for 1 h;Inert atmosphere;
Stage #3: with p-nitrobenzenesulfonyl azide;triethylamine in tetrahydrofuran;hexane;water;acetonitrile at 20; for 12 h;Inert atmosphere;
Steps:
allyl 2-diazoacetate (4a)
To a stirred solution of allyl acetate (3.2 mL, 29.9 mmol) in THF (299 mL) was added a solution of LiHMDS (1.06 M in n-hexane, 31.2 ml, 34.4 mmol) dropwise at -78 °C. The resulting solution was stirred at -78 °C for 30 min and then was treated with 2,2,2-trifluoroethyl trifluoroacetate (4.5 mL, 33.7 mmol). The resulting solution was stirred at -78 °C for 1 h and then tothe solution was added deionized H2O (5.3 mL, 299 mmol). After 10 min, the solution was dissolved in CH3CN (20 mL) and to the resultant solution was added a solution of p-nitrobenzenesulfonyl azide (6.8 g, 29.9 mmol) in CH3CN (20 mL), and then, Et3N (16.7 mL, 119.6 mmol) were added. The resultant solution was stirred at room temperature for 12 h and was then concentrated to a volume of ca. 10 mL. The residue was diluted with 30 ml of Et2O, quenched with 10% NaOH aqueous solution (20 mL), extracted with Et2O (20 mL×3). The combined organic layer was washed with brine (50 mL×1), dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography (hexane only) to afford the known diazo ketone 38 (2.45 g, 65%)
References:
Inoue, Saori;Nagatani, Kotaro;Tezuka, Haruka;Hoshino, Yunosuke;Nakada, Masahisa [Synlett,2017,vol. 28,# 9,art. no. ST-2016-U0854-L,p. 1065 - 1070] Location in patent:supporting information
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