Organic Process Research Development Article Table 1.'H NMR Data proton mult,/ CDCh acetone-d. DMSO.d CDCN CDOD D.O solvent residual peak 726 205 250 1.94 3.31 4.79 water A HO 1.56 2.84 3.33 2.13 4.87 acetic acid CH 2.10 196 1q1 1.96 1.99 2.08 acetic anhydride A CH 9 2.23 2.21 222 2.18 acetone" ▲CH 2.17 2.09 2.09 2.08 2.15 2.22 acetonitrile" CH 2.10 2.05 2.07 1.96 2.03 2.06 iso-amyl acetate ▲OCH t6.8 4.10 4.05 4.02 4.05 4.09 4.14 CHCO 2.05 1.97 1.99 1.97 2.01 2.07 CH nonet.6.7 1.68 1.69 1.64 1.67 1.69 1.67 CH-CH 96.9 1.52 1.50 1.45 1.49 1.51 1.53 (CH d.6.6 0.92 091 0.88 0.91 0.93 0.89 iso-amyl alcohol ▲CHOH td68.52 3.68.1(6.8) 3.563.55,f 341 3.51 3.57.t(6.9) 3.64.t(6.8) OH t.52 334 429 2.40 CH nonet,6.7 1.72 173 1.65 1.67 171 1.67 CH-CH 9.6.8 147 139 131 137 142 1.44 CHi d.6.7 0.92 0.89 0.85 0.89 0.91 0.90 anisole ▲CH(3.5) m 732-727 731-7.25 7.31-7.26 732-727 7.28-7.22 7.40,t(8.0y CH(2.4.6) 6.97-6.89 6.96-6.89 6.94-6.90 6.96-6.90 6.92-6.87 7.09-7.03 OCH 3.81 3.78 3.75 277 3.77 3.85 benzyl alcohol A CH 738-7.28 737-7.29 7.36-728 7.37-7.30 7.36-7.30 7.47-737 CH 738-7.28 725.7.20 7.25-7.20 729-7.23 7.26-7.22 7.47-7.37 CH2 d.59 4.71 4.634.62.s 4.49 4.57 4.59.s 465.5 OH 5.9 1.64 4.16 5.16 3.14 n-butanol ▲CH,OH td6.5.53 3.65.t6.7 3.533.52,tf 3.38 3.48 3.54.t(6.5) 3.61.t(6.6) CH:CHOH m 1.60-1.52 L51-144 1.43-1.25 1.49-1.42 1.55-1.47 1.57-1.50 CHCH m 144-135 141-132 1.43-1.25 1.39.129 1.43-1.33 1.40-1.30 OH t5.3 1.20.br s 3.35 4.31 2.43 CH. t7.3 0.94 0.90 086 0.91 0.93 0.91 iso-butanol A CH: dd.65.5.5 3.41 3.29 3.15 3.25 3.31-3.29.m 338.d(6.6) CH nonet,6.6 1.77 1.68 1.60 1.66 1.70 1.75 OH t5.5 130 3.45 4.40 2.50 CH d,6.7 0.92 0.87 0.82 0.86 0.90 0.89 tert-butanol A CHs 5 1.27 1.1811.181 1.11 1.17 1.22 1.25 OH 322 4.18 239 n-butyl acetate ▲OCH2 t6.7 4.07 4.02 3.99 4.02 405 4.12 2.05 1.97 1.99 1.97 2.01 2.09 OCHCH. m 1.64-1.57 1.62-155 1.57-1.50 1.61-154 1.64-1.57 1.67-1.60 m 1.43-1.34 L.42-1.33 1.37-127 1.41-1.32 144-1.34 1.42-1.33 CHCH t7.4 0.94 0.92 0.89 0.92 0.94 0.91 iso-butyl acetate d.6.7 3.85 3.81 3.79 3.81 3.84 3.91 CHCO 2.06 1.99 2.01 1.99 2.03 21 CH nonet,6.7 1.92 1.89 1.87 1.90 1.92 1.94 (CH方 d6.7 0.93 0.91 0.88 0.91 093 093 chlorobenzene CH m 7.36-1.22 7.42-7.31 7.45-7.32 7.41-729 7.37-725 7.46-7.33 cyclohexane" CH. 1.43 143 140 1.44 145 cyclohexanone ▲CH(2.6 L7 233 2.27 2.25 2.27 2.34 2.40 CH(3.5 m 1.86-1.84 183-1.79 1.78-1.74 1.84-1.79 187-185 1.90-1.85 H(4) m 1.73-1.71 1.74-170 1.66-1.64 1.72-1.67 1.76-1.74 1.75-1.70 cyclopentyl methyl ether CH 3.82-3.78 3.77-3.73 3.76-3.71 3.78-3.74 3.85-3.80 3.99-3.94 (CPME) OCHs 3.28 3.19 3.15 3.19 326 3.30 1.74-1.50 1.72-1.44 1.67-1.42 1.70-1.48 1.77-1.50 1.86-1.51 p-cymene 章ArH m 7.14-7.09 7.13-7.07 7.12-7.07 7.14-7.09 7.09-7.04 (4-iso-propyltoluene) CH(CHh sept,6.9 2.87 285 2.83 2.86 2.83 Ar-CH: 232 227 2.25 2.28 227 、 (CH) d.6.9 124 120 1.17 1.20 1.21 、 dichloromethane" CH, 5.30 5.63 5.76 5.44 5.49 dimethyl carbonate" 4 CHy 3.79 3.72 3.69 3.72 3.74 3.69 dimethyl sulfoxide" CHi 2.62 252 2.54 2.50 265 2.71 DMPU NCH m 325-3.22 3.25-322 320-3.17 3.22-3.19 330-3.27 3.30-327 NCH 2.92 281 2.75 2R1 288 2R6 CH 2.00-1.94 L97-1.92 1.90-1.84 1.94-1.88 2.00-1.94 1.98-192 ethanol A CH qd.7.0,52 3.72.q(7.0) 3573.57,q 344 3.54 3.60.9(7.1) 3.66.q(71) CHs t.7.0 124 1.12[1.12] 1.06 L.11 1.17 1.19 OH t52 1.42,br s 3.39 4.35 2.47 ethyl acetate" A CH.CO 2.03 197 199 1.97 2.01 2.07 q,7 4.12 4.05 4.03 4.06 4.09 4.14 CH-CH, t.7 1.26 120 117 120 1.24 1.24 L-ethyl lactate CH 9.6.9 4.30-4.22.m 4.24-4.09,m4.144.08.m4.21-4.11,m 4.22 4.40 CH q.7.1 425 424-4.09.m 4.08 421-4.11.m 4.18 4.23 OH d.5.5 2.79 535 3.33 CHCH d.6.9 1.42 1.32 124 131 1.36 1.41 CHCH: t7.1 131 123 1.19 1.23 127 1.28 ethylene glycol ▲CH 3.76 3.58-3.54.m340-3.38,m3.52-3.50,m 359 3.67 OH 2.28.br 5 446-4.43 2,72-2.69 662 D0t10.1021/as.oprd5b00417 Org.Process Res.Dev.2016,20,661-667Table 1. 1 H NMR Data Organic Process Research & Development Article DOI: 10.1021/acs.oprd.5b00417 Org. Process Res. Dev. 2016, 20, 661−667 662