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(i) 4-Methylbenzaldehyde (1.5 equiv), AcOH (0.5 equiv), NaBH(OAc)3, CH2Cl2, 0 °C to rt, 48 h; (ii) LiAlH4 (1 M in THF, 3.5 equiv); (iii) chloroacetyl chloride (2.0 equiv), NEt3 (2.0 equiv), THF, 0 °C to rt, 16 h; (iv) NaOH (10 N, aq.), rt, 2 h; (v) 4-pyridyl-B(OH)2 (1.1 equiv), Pd(dppf)Cl2 (5 mol %), K2CO3 (3.0 equiv), 1,4-dioxane/H2O (4:1), 90 °C, 18 h.
