[CH3:1][C:2]#[N:3].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:14]([CH:17]([CH2:29][CH2:30][CH3:31])[CH2:18][O:19][C:20]1[O:24][C:23]([C:25](OC)=[O:26])=[CH:22][CH:21]=1)[CH2:15][CH3:16]>C1COCC1>[O:26]=[C:25]([C:23]1[O:24][C:20]([O:19][CH2:18][CH:17]([CH2:29][CH2:30][CH3:31])[CH2:14][CH2:15][CH3:16])=[CH:21][CH:22]=1)[CH2:1][C:2]#[N:3]Anhydrous CH3CN (0.15 mL, 2.87 mmol) was added to a solution of LiHMDS (1M/THF, 3.0 mL, 3.0 mmol) at −75° C. under inert atmosphere and the reaction mixture was stirred for 5 min. A solution of methyl 5-((2-propylpentyl)oxy)furan-2-carboxylate (1.337 mmol) in anhydrous THF (7 mL) was added to the reaction mixture and the reaction mixture was stirred under inert atmosphere while slowly warming to 0° C. for over 75 min. The reaction mixture was partitioned between aqueous NaHSO4 (10%) and EtOAc. Organic layer was washed with brine, concentrated under reduced pressure. Flash chromatography purification (10%-50% EtOAc—hexanes gradient) gave 3-oxo-3-(5-((2-propylpentyl)oxy)furan-2-yl)propanenitrile as an off-white solid. Yield (0.23 g, 66%); 1H NMR (400 MHz, DMSO-d6) δ 7.57 (d, J=3.8 Hz, 1H), 5.78 (d, J=3.8 Hz, 1H), 4.30 (s, 2H), 4.08 (d, J=5.6 Hz, 2H), 1.69-1.79 (m, 1H), 1.23-1.35 (m, 8H), 0.80-0.88 (m, 6H).
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