[CH3:1][O:2][CH2:3][C:4]([CH2:6][O:7][CH3:8])=[CH2:5].B.C1C[O:13]CC1.B(O[O-])=O.[Na+]>C1COCC1.C(Cl)Cl>[CH3:1][O:2][CH2:3][CH:4]([CH2:6][O:7][CH3:8])[CH2:5][OH:13]To a solution of the 3-methoxy-2-methoxymethyl-1-propene (3.5 g, 30 mmol, 1.0 eq.) in THF (10 mL) at 0° C. was added BH3.THF (1M in THF, 18 mL, 0.6 eq.) and the resulting mixture was stirred for 40 min. The reaction was quenched with water followed by sodium perborate (10.6 g, 2.3 eq.), warmed to room temperature, stirred overnight, diluted with CH2Cl2 and filtered through celite. The filtrate was diluted with brine and the separated aqueous layer was extracted with CH2Cl2. The combined extracts were dried over Na2SO4 and filtered. The filtrate was distilled at atmospheric pressure to give light yellow liquid residue. Fractional distillation of the residue at 40 milliTorr gave 3-methoxy-2-methoxymethypropan-1-ol (1.93 g, 48%). b.p.=90-110° C.
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