Iodine → HCID 11623636, compound

Participants

Reaction Conditions

Reaction Steps

63.4 mg (0.2 mmol) of 5 and 27 mg (0.6 mmol) sodium borohydride were dissolved in 3 mL of THF. After the solution was cooled to 0° C., 51 mg (0.2 mmol) I2 was dissolved in 1 mL THF and added dropwise. Then the vessel was fitted with a condenser and the reaction mixture was refluxed under N2 for 5 hrs. Excess NaBH4 was quenched with methanol. After removal of solvent, 2 mL water and 5 mL methylene chloride was added, the mixture was stirred for about 1 hr until the organic layer became clear. The organic phase was collected and aqueous phase was further extracted twice with methylene chloride. The combined organic extraction was dried and concentrated to provide 43 mg (71%) of the crude product. Further purification on TLC with methanol/chloroform (5:95) provided 13 mg of clear oil. J. Org. Chem., 1993, 58, 3568-3571. 1H NMR (CD3OD) δ 7.11 (m, 4H, ArH), 3.80 (t, J=7.5 Hz, 1H, c-pentyl-CH2O), 3.67 (t, J=7.5 Hz, 1H, c-pentyl-CH2O), 3.01 (m, 1H, ArCHCC), 2.55 (t, J=7.5 Hz, 2H, ArCH2), 2.29-1.69 (m, 6H, cyclo-pentyl), 1.57 (m, 2H, ArCH2CH2), 1.38-1.28 (m, 10H, CH2), 0.89 (t, J=7.5 Hz, 3H, CH3); 13C NMR (CD3COCD3) δ 141, 128, 127, 96, 45, 44, 43, 35, 35, 33, 33, 32, 32, 29, 29, 29, 23, 13.

Provenance & Evidence