D-(+)-MALIC ACID DIMETHYL ESTER synthesis
- Product Name:D-(+)-MALIC ACID DIMETHYL ESTER
- CAS Number:70681-41-3
- Molecular formula:C6H10O5
- Molecular Weight:162.14
67-56-1
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70681-41-3
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Yield:70681-41-3 99%
Reaction Conditions:
with thionyl chloride at 0 - 20;Inert atmosphere;
Steps:
(R)-Dimethyl 2-hydroxysuccinate (5)
SOCl2 (2.40 mL) was added dropwise to a solution of (R)-malic acid 4 (2.0024 g, 15 mmol) in MeOH (20 mL) at 0oC. The solution was stirred at room temperature for 24 hours then concentrated under reduced pressure. Flash chromatography (1:1 EtOAc:Pet ether) gave 5 (2.4034 g, 99%) as a light yellow oil, with spectral data in accordance with the literature [6, 7]. Rf (1:1 EtOAc:Pet ether): 0.30. 1H NMR (500 MHz, CDCl3) ppm 4.52 (q, J = 5.5 Hz, 1H, H2), 3.82 (s, 3H, OCH3), 3.72 (s, 3H, OCH3), 2.95-2.74 (m, 2H, H3). 13C NMR (126 MHz, CDCl3) d ppm 173.9, 171.2, 67.4, 53.1, 52.2, 38.6. HRMS (ESI): Calcd. for C6H10NaO5 [M+Na]+: 185.0420; found: 185.0427.
References:
Tran, David;Pietersma, Amy L.;Schofield, Linley R.;Rost, Matthias;Jameson, Geoffrey B.;Parker, Emily J. [Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,# 22,p. 6838 - 6841] Location in patent:supporting information; experimental part
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70681-41-3
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67-56-1
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553-90-2
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70681-41-3
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70681-41-3
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