[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:5]=1[CH:6]=[O:7].[CH3:13][O:14][CH2:15][CH2:16][O:17][CH2:18]OCl.[BH4-].[Na+].Cl>C1COCC1.O.CCOCC.CN1CCCN(C)C1=O>[I:12][C:9]1[CH:10]=[CH:11][C:4]([O:3][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:5]([CH:8]=1)[CH2:6][OH:7]To a solution of sodium hydride (1.2 g of a 60% mineral oil dispersion, 52 mmol) in 25 mL of THF at 0° C., is added 2-hydroxy-5-iodo-benzaldehyde (7.0 g, 28 mmol). To the resulting solution is added 2-methoxy-ethoxymethoxy chloride (3.4 mL, 30 mmol) and 4 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone. The solution is allowed to warm to ambient temperatures. After 45 min., the solution is cooled to -15° C. and 6 mL of a 2M solution of sodium borohydride in THF is added. The solution is stirred for 10 min. After this time, 24 mL of a 2M HCl solution in water is added. The resulting solution is diluted with ether, washed with water and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The resulting crude material is purified by column chromatography eluting with 40% EtOAc/hexanes to give the title compound (7.6 g, 22.5 mmol) as a white solid.
Loading…
