HCID 5372577, compound → HCID 12840254, compound
Reaction equation
[CH:1]([Mg]Br)([CH3:3])[CH3:2].[C:6]([O:16][CH3:17])(=[O:15])/[CH:7]=[CH:8]/[CH2:9][CH2:10][C:11]([O:13]C)=O>C1COCC1>[CH:1]([CH:8]1[CH2:9][CH2:10][C:11](=[O:13])[CH:7]1[C:6]([O:16][CH3:17])=[O:15])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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).