ETHYL 3-METHYL-2-BUTENOATE-D6 synthesis
- Product Name:ETHYL 3-METHYL-2-BUTENOATE-D6
- CAS Number:53439-15-9
- Molecular formula:C7H6D6O2
- Molecular Weight:134.2059
Yield:53439-15-9 86.6%
Reaction Conditions:
with n-butyllithium in tetrahydrofuran;hexane at -5 - 20;
Steps:
1.1-2.1 1) Step 1: Preparation of [4,4'-2H6]-ethyl-3-methyl-2-butenoic acid ethyl ester
Triethyl phosphonoacetate (39.3g, 0.176mol), dry tetrahydrofuran (350ml), cool to -50, slowly drop in n-butyllithium (0.16mol, 2.5M n-hexane solution), and gradually heat to Stir at room temperature until the bubbling stops. A solution of deuterated acetone (7.5g, 0.117mol) in 70ml of dry tetrahydrofuran is added to the phosphonic acid anion solution. The mixture is stirred at room temperature for 44.5h. TLC identifies the end point (pentane/ Diethyl ether = 2:1), then add 22ml saturated ammonium chloride solution to quench, extract the aqueous layer with isopropyl ether, combine the organic layers, wash with brine (30mL×3), dry with anhydrous magnesium sulfate, filter out the desiccant, The filtrate was concentrated under reduced pressure, and the crude product was purified by column chromatography (pentane/ether=2:1) to obtain 13.6 g of light yellow oily target compound with a yield of 86.6% and a GC content of 97.8%.
References:
CN111217749,2020,A Location in patent:Paragraph 0031-0038; 0064-0066