[BH4-].[Na+].[CH2:3]([O:10][CH2:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][C:15]=1[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CO.[Cl-].[NH4+]>C1COCC1>[CH2:3]([O:10][CH2:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][OH:19])=[CH:16][C:15]=1[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1To a stirred mixture of 1.00 g (26.5 mmol) sodium borohydride in 80 ml THF was added 2, 0.9 g (8.83 mmol) 4-[2-(benzyloxy)ethoxy]-3-tert-butoxybenzaldehyde diluted in 40 ml THF drop by drop. The reaction mixture was stirred for 10 min. Methanol (5.8 ml) was added to this mixture drop by drop. The reaction mixture was stirred for 2 hours and poured onto ˜200 ml stirred ice-cooled saturated aqueous ammonium chloride solution. The solution was extracted trice with dichloromethane. The combined organic phases were dried with sodium sulfate and concentrated in vacuo. The crude product was used in the following reaction without further purification.
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