Methyl 2,2-dithienylglycolate synthesis
- Product Name:Methyl 2,2-dithienylglycolate
- CAS Number:26447-85-8
- Molecular formula:C11H10O3S2
- Molecular Weight:254.32
1003-09-4
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26878-13-7
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$220.00/100mg
26447-85-8
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$6.00/1g
Yield:26447-85-8 75%
Reaction Conditions:
Stage #1: 2-bromothiophenewith n-butyllithium in tetrahydrofuran; for 0.333333 h;Inert atmosphere;Cooling;
Stage #2: methyl 2-thienylglyoxylate in tetrahydrofuran; for 0.5 h;Inert atmosphere;Cooling;
Steps:
Lithiation of 2-Bromothiophene: preparation of oxo-acetate (4a,c) and glycolates (1a,b).
General procedure: In a flame-dried round flask, organolithium reagent (0.95 mmol) was added dropwise to a solution of 2-bromothiophene 1b (193 mg, 1.0 mmol) in anhydrous THF (15 mL) under N2 at -80 °C. After 20 min, a THF (5.0 mL) solution of oxalate 3 or oxo-acetate 4a-c was added. After the disappearing of the starting thiophene, the reaction was quenched by saturated aqueous NH4Cl and extracted with AcOEt (2×20 mL); the collected organic phases were washed with brine (1×10 mL), dried over Na2SO4 and the solvent was evaporated under vacuum (RV). The resulting crude was purified by FCC - AcOEt/hexane (1:9) - on silica gel. Yield, physical, spectroscopic and analytical data of products 4a,c, 1a,b are as follows.
References:
Foschi, Francesca;Bonandi, Elisa;Mereu, Andrea;Pacchetti, Barbara;Gozzini, Davide;Passarella, Daniele [Arkivoc,2018,vol. 2018,# 7,p. 423 - 430]
1003-09-4
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553-90-2
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26447-85-8
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553-90-2
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5713-61-1
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26447-85-8
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64-19-7
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26447-85-8
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704-38-1
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26447-85-8
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