The Preparation of Substituted Hydroxyphenyl-pyridyl-ethanols and α-Hydroxyphenyl-α-methylpyridineethanols by the Condensation of 2-, 3-, or 4-Picolyllithium with Select Hydroxy-benzaldehydes and 4-Hydroxyacetophenone

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• Infrared spectra were obtained from a Mattson Polaris FT-Infrared Spectrometer. 1H nmr for 1–10 and 12 were obtained from a Varian Associates, EM-360L Nuclear Magnetic Resonance Spectrometer, and chemical shifts are reported in δ ppm downfield from an internal tetramethylsilane (TMS) standard. The 1H nmr for compound 11 was obtained from a 400 MHz, Varian Associates VXR multi-probe nuclear magnetic resonance spectrometer. Compound No., ir; nmr: Compd. 1; ir (paraffin oil) 3400 cm−1 broad and shoulder (OH); nmr (DMSO-d6), δ 2.58–2.93 (m, CH2), 4.88–5.27 (m, CH), 6.53–7.70 and 8.18–8.52 (m, ArH), and 9.47 (s, ArOH). Compd. 2; ir (paraffin oil) 3503 cm−1 broad and shoulder; nmr (DMSO-d6 and CDCl3), 2.93 (d, CH2), 4.75 (t. CH), 6.58–7.42 and 8.25–8.55 (m, ArH). Compd. 3; ir (paraffin oil) 3380 cm−1 broad and shoulder (OH); nmr (DMSO-d6), 2.88 (d, CH2), 4.95–5.23 (m, CH), 6.50–7.23 and 8.20–8.50 (m, ArH), and 9.23 (s-broad, ArOH). Compd. 4; ir (paraffin oil), 3200 cm−1(shoulder of paraffin oil absorption); nmr (DMSO-d6), 3.00 (d, CH2), 4.67–5.13 (m, CH), 6.43–7.83 and 8.40–8.63 (m, ArH), and 9.27 (s, ArOH). Compd. 5; ir (KBr), 3427 and 3557 cm−1(OH and ArOH); nmr (DMSO-d6 and CDCl3), 2.90 (d, CH2), 4.75 (t, CH), 6.58–7.37 and 8.37–8.57 (m, ArH). Compd. 6; ir (KBr), 3418 cm−1; nmr (DMSO-d6), 3.02 (d, CH2), 4.90 (t, CH), 6.33–7.93 and 8.30–8.67 (m, ArH), and 9.19 (s broad, ArOH). Compd. 7; ir (paraffin oil), 3166 cm−1(OH, with shoulder); nmr (DMSO-d6 and CDCl3), 1.43 (s, CH3), 2.47 (s, CH2), 3.17(s, OH), 6.60–.95 and 8.40–8.57 (m ArH). Compd. 8; ir (paraffin oil), 3511 (sh,OH from H2O), and 3332 and 3148 cm−1(shoulders of paraffin oil absorption); nmr (DMSO-d6 and CDCl3), 1.48 (s, CH3), 2.97 (s, CH2), 6.62–7.33 and 8.20–8.45 (m, ArH). Compd. 9; ir (KBr), 3460 cm−1; nmr (DMSO-d6), 2.85 (d, CH2), 3.73 (s, OCH3) 4.67 (t, CH), 6.57–7.33 and 8.27–8.58 (m, ArH), and 8.67–9.05 (bm, ArOH). Compd. 10; ir (paraffin oil), 3200–3300 cm−1(OH, shoulder of paraffin oil absorption); nmr (DMSO-d6), 2.99 (d, CH2), 3.72 (s, OCH3), 5.10 5.33 (m, CH), 6.68–7.77 and 8.42–8.58 (m, ArH), and 8.88 (s-broad, ArOH). Compd. 11; nmr (DMSO-d6), δ 7.06 (s, vinyl, J = 17), 7.14(s, vinyl, J = 17), 7.89 (dd, J = 1.5 and 5, H-2 pyridyl ring), 8.50 (d. J = 0 and 1.8, H-6 pyridyl ring), 6.80–7.38 (other ArH), and 8.76 (s, ArOH). Compd. 12 3–8.17 and 8.43–8.93 (vinyl and ArH), and 10.33 (s, ArOH)
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• Microanalyses for C, H, and N were obtained from Quantitative Technologies, Inc., Box 470, Salem Industrial Park, Whitehouse, NJ 07940 [Compd. No. from Table]. Calcd. for 1: C, 72.54; H, 6.09; N, 6.51. Found: C, 72.56; H, 6.11; N, 6.38. Calcd. for 1: C, 72.54; H, 6.09; N. 6.51. Found: C, 72.27; H, 6.34; N, 6.17. Calcd. for 3: N, 6.51. Found: N. 6.45. Calcd. for 4: C, 72.54; H, 6.09; N, 6.51. Found: C, 72.19; H, 6.04; N. 6.42. Calcd. for 5: C, 72.54; H, 6.09; N, 6.51. Found: C, 72.63; H, 6.08; N. 6.40. Calcd. for 6: C, 72.54; H, 6.09; N, 6.51. Found: C, 72.71: H. 6.20; N. 6.32. Calcd. for 7: C, 73.34; H, 6.59; N. 6.11. Found: C, 72.95: H. 6.59; N. 6.00. Calcd. for 8 (C14H15NO2.H2O): C, 68.00: H, 6.93; N. 5.66. Found: C, 68.00; H, 6.81; N, 5.47. Calcd. for 9 C. 68.28: H. 6.14: N, 5.69. Found: C, 68.43; H, 6.15; N, 5.61. Calcd. for 10: C, 68.54; H, 6.15: N. 5.73. Found: C, 68.42; H, 6.25; N, 5.68. Calcd. for 11 (C13H11NO. 1/2 H2O): C, 75.71; H,5.86; N, 6.79. Found: C, 76.93; H, 5.91; N, 6.67. Calcd. for 12 (C13H10BrNO): C, 56.55; H, 3.65; N, 5.07. Found: C, 56.46; H, 3.57; N, 4.85.
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• Separate grants: The scope of this collaborative project is in addition to the proposed and approved studies of each investigator
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• NSF-ILI grant number 9250209.
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