C(P([CH2:8][C:9]([O-:11])=[O:10])(CC)CC)C.[H-].[Na+].[CH:14]1([CH:20]=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[Cl-].[NH4+].[CH2:24]1COC[CH2:25]1>CCCCCC>[CH2:24]([O:11][C:9](=[O:10])/[CH:8]=[CH:20]/[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[CH3:25]Add triethylphospinoacetate (185 g, 821 mmol) to a suspension of hexane-washed sodium hydride (34.5 g, 60%, 862 mmol) in THF (1 L) at 0° C. Stir the resulting mixture for 1 h, and then cool it to −78° C. Then add a solution of cyclohexylmethanal (92.2 g, 821 mmol) in THF (500 mL) dropwise over 90 min, maintaining an internal temperature of less than −68° C. Allow the reaction mixture to warm to r.t. over 18 h. Then add a solution of saturated aqueous ammonium chloride solution (1 L) to the reaction mixture carefully. Extract the resulting mixture with ether (3×1 L). Combine the extracts and wash them with water (2×1 L), followed by saturated aqueous sodium chloride solution (1 L). Then dry the extracts over magnesium sulfate, and concentrate the solution under vacuum to afford the title compound as a yellow oil (154.8 g). GC-MS (m/e): 182 (M+).
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