HCID 5372577, compound → HCID 12840254, compound

Temperature

0 °C

An isopropylmagnesium bromide (58 mL, 58 mmol) solution (15% in THF, ˜1 M) was treated with Cu(I)I (0.28 g, 1.5 mmol) and cooled to 0° C. A solution of (E)-dimethyl hex-2-enedioate (5.0 g, 29 mmol; See Example 80, Step 1) was added dropwise, and the solution was stirred at 0° C. for an additional 30 minutes and then at room temperature. The product was poured into saturated NHCl4 (250 mL) with rapid stirring. The mixture was extracted into DCM. The combined organics were back extracted with H2O, and dried with MgSO4, filtered, and concentrated under reduced pressure to yield methyl 2-isopropyl-5-oxocyclopentanecarboxylate (5.4 g, 100%), which was used without further purification. 1H NMR (CDCl3, 400 MHz) δ 3.76-3.73 (m, 3H), 2.94-2.91 (m, 1H), 2.48-2.16 (m, 2H), 1.87-1.84 (m, 2H), 1.68-1.43 (m, 2H), 0.97-0.84 (m, 6H).

1. customat room temperature
2. extractionThe mixture was extracted into DCM
3. extractionThe combined organics were back extracted with H2O
4. dry with materialdried with MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure

ORD record

ord-e5a3c5a08445476fb92f9afa7b4fab72

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324221B2