Hydrochloric Acid → HCID 23500391, compound

Temperature

-78 °C

A solution of malonic acid monoethyl ester (16.9 g, 128 mmol) in dry THF (200 mL) was cooled to -78° C. under nitrogen, treated dropwise with 130 mL of isopropyl magnesium chloride (2.0M in THF; 260 mmol), and stirred at -78° C. for 45 minutes. A solution of 3-(4-nitrophenyl)propanoyl chloride prepared in Example EE (13.5 g, 64 mmol) in dry THF (100 mL) was added dropwise. When addition was complete, the reaction mixture was stirred at -78° C. for 1 hour and then allowed to warm to room temperature, where the solution was stirred for 3 more hours. A mixture of ice (50 mL) and 3N HCl (100 mL) was added. The solution was extracted with EtOAc, and the combined extracts were washed with brine and dried (MgSO4). Concentration gave the title compound. 1H NMR (CDCl3) δ 1.21 (t, 3 H), 2.88-3.00 (m, 4 H), 3.40 (s, 2 H), 4.13 (q, 2 H), 7.3 (d, 2 H), 8.09 (d, 2 H).

1. additionwas added dropwise
2. additionWhen addition
3. stirringthe reaction mixture was stirred at -78° C. for 1 hour
4. temperatureto warm to room temperature
5. stirringwhere the solution was stirred for 3 more hours
6. additionwas added
7. extractionThe solution was extracted with EtOAc
8. washthe combined extracts were washed with brine
9. dry with materialdried (MgSO4)
10. concentrationConcentration

ORD record

ord-0b94f7fb660b4886bfcd841c06911a67

Source dataset

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05834506