Dibenzyl cyclohexane-1,1-dicarboxylate → HCID 18623884, compound
Reaction equation
[C:1]1([C:17](OCC2C=CC=CC=2)=[O:18])([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[CH:17]([C:1]1([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of dibenzyl cyclohexane-1,1-dicarboxylate (10.5 g, 30 mmol, from Step A) in 100 mL CH2Cl2 was cooled to −78° C. and a solution of diisobutylaluminum hydride (60 mL, 1 M in CH2Cl2, 60 mmol) was added dropwise. After 3.5 h the mixture was carefully quenched with sat'd ammonium chloride and 1 M HCl. The mixture was warmed to rt and poured into 200 mL water and 200 mmL CH2Cl2. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over magnesium sulfate and concentrated. Flash chromatography (400 g silica, 10/1 hexane/EtOAc) gave 5.9 g (79%) of the desired aldehyde. 1H NMR (500 MHz, CDCl3) δ1.4-1.6 (m, 16), 1.88-1.95 (m, 2H), 2.03-2.12 (m, 2H), 5.2 (s, 2H), 7.30-7.41 (m, 5H), 9.58 (s, 1H).