Dimethyl malonate → HCID 67523648, compound

Temperature

0 °C

To a mixture of O-acetylsalicyloyl chloride (Alfa Aesar, 1.0 g, 5.05 mmol) in THF (10 mL) at 0° C. was added sodium hydride (60% dispersed in mineral oil, 263 mg, 6.57 mmol). It was stirred at 0° C. for 15 min prior to the addition of a solution of dimethyl malonate (0.67 g, 5.05 mmol) in THF (5 mL) at 0° C. The resulting mixture was stirred at 0° C. for 5 min and then at rt for 2.5 h, and was concentrated. The residue was taken up in water (50 mL), acidified by 1 N HCl aqueous solution, and extracted with EtOAc (2×100 mL). Combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to give the intermediate (2-(2-acetoxy-benzoyl)-malonic acid dimethyl ester) (1.45 g) as an oil. The intermediate (1.26 g, 4.28 mmoL) was treated with (1/1) MeOH/10% aq HCl (26 mL) and heated to 75° C. (oil bath temperature) for 30 min and then at rt overnight. White precipitate formed during the reaction was collected, rinsed with water and dried in vacuo to give the title compound (555 mg). MS ESI(+) m/e: 221 (M+1).

1. stirringThe resulting mixture was stirred at 0° C. for 5 min
2. waitat rt for 2.5 h
3. concentrationwas concentrated
4. extractionextracted with EtOAc (2×100 mL)
5. washCombined organic layers were washed with brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-bb4fed49587e48afb2026de797e3f77a

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324405B2