The Journal of Organic Chemistry
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2399, 1508, 1215, 1022, 815, 752, 669, 572, 499; HRMS (ESI) calcd for
C18H21O 253.1592, found 253.1586.
7.09 (m, 1H), 2.49 (s, 1H), 1.43-1.37 (m, 1H), 0.85-0.81 (m, 1H),
0.71-0.67 (m, 1H), 0.63-0.57 (m, 2H); 13C NMR (CDCl3, 125 MHz)
δ143.4, 133.5, 129.9, 129.3, 128.3, 127.0, 125.5, 121.1, 88.2, 81.4, 74.4, 23.8,
3.3, 2.5.
Cyclopropylbis(4-methoxyphenyl)methanol (1g): yield 87%;
colorless oil; 1H NMR (CDCl3, 300 MHz) δ 7.38-7.33 (m, 4H), 6.86-
6.81 (m, 4H), 3.79 (s, 6H), 1.94 (s, 1H), 1.64-1.44 (m, 1H), 0.64-0.46
(m, 2H), 0.42-0.29 (m, 2H); 13C NMR (CDCl3, 75 MHz) δ 158.4, 139.7,
128.0, 113.1, 76.6, 55.2, 21.8, 1.7; IR (neat, cm-1) 3541, 3431, 3018, 1635,
1508, 1215, 1035, 779, 671, 522; HRMS (ESI) calcd for C18H21O3
285.1491, found 285.1494.
(4-Chlorophenyl)(cyclopropyl)(p-tolyl)methanol (1h): yield
76%; colorless oil; 1H NMR (CDCl3, 400 MHz) δ 7.35-7.10 (m, 8H),
2.32 (s, 3H), 1.85 (s, 1H), 1.58-1.51 (m, 1H), 0.63-0.39 (m, 4H); 13C
NMR (CDCl3, 100 MHz) δ 146.0, 143.9, 137.0, 132.7, 128.8, 128.2, 127.9,
126.8, 76.7, 21.5, 21.0, 2.0, 1.5; IR (neat, cm-1) 3008, 1489, 1215, 1091,
1014, 819, 756, 667, 509; HRMS (ESI) calcd for C17H18OCl 273.1046,
found 273.1041.
(4-Chlorophenyl)(cyclopropyl)(4-methoxyphenyl)methanol
(1i): yield 84%; light brown oil; 1H NMR (CDCl3, 400 MHz) δ 7.27-
7.15 (m, 6H), 6.7 (d, 2H, J = 8.5 Hz), 3.6 (s, 3H), 2.13 (s, 1H), 1.49-1.42
(m, 1H), 0.55-0.34 (m, 4H); 13C NMR (CDCl3, 100 MHz) δ 158.7,
146.1, 139.1, 132.6, 128.2, 127.9, 113.3, 76.5, 55.2, 21.7, 2.1, 1.4; IR (neat,
cm-1) 3585, 3446, 1608, 1510, 1249, 1176, 831, 586, 499; HRMS (ESI)
calcd for C17H18O2Cl 289.0995, found 289.0989.
Cyclopropyl(phenyl)(p-tolyl)methanol (1j): yield 84%; color-
less oil; 1H NMR (CDCl3, 400 MHz) δ 7.33 (d, 2H, J = 7.8 Hz), 7.22-
7.09 (m, 5H), 7.00 (d, 2H, J = 7.8 Hz), 2.21 (s, 3H), 1.83 (s, 1H), 1.51-
1.44 (m, 1H), 0.49-0.35(m, 4H);13CNMR(CDCl3, 100MHz) δ147.5,
144.4, 136.6, 128.7, 127.9, 126.98, 126.92, 126.8, 77.0, 21.7, 21.1, 1.9, 1.7;
IR (neat, cm-1) 3356, 3010, 1647, 1510, 1446, 1215, 981, 815, 752, 667,
514; HRMS (ESI) calcd for C17H19O 239.1436, found 239.1430.
Cyclopropyl(phenyl)(4-biphenyl)methanol (1k): yield 68%;
white solid; mp 92-94 °C; 1H NMR (CDCl3, 300 MHz) δ 7.50-7.24
(m, 14H), 1.93 (s, 1H), 1.71-1.62 (m, 1H), 0.65-0.58 (m, 2H), 0.54-
0.49 (m, 2H); 13C NMR (CDCl3, 75 MHz) δ 147.2, 146.3, 140.8, 139.8,
128.7, 128.0, 127.3, 127.2, 127.0, 126.8, 126.6, 21.6, 1.85, 1.83; IR (neat,
cm-1) 3392, 3018, 1645, 1487, 1446, 1215, 1031, 839, 748, 700, 667, 628,
622, 514, 499; HRMS (ESI) calcd for C22H20ONa 323.1412, found
323.1404.
1-Cyclopropyl-1-(4-methoxyphenyl)-3-(pyridin-2-yl)prop-
2-yn-1-ol (1p):9c yield 69%; light brown solid; 1H NMR (CDCl3, 500
MHz) δ 8.53-8.52 (m, 1H), 7.68-7.66 (m, 2H), 7.63-7.59 (m, 1H),
7.39 (d, 1H, J = 7.8 Hz), 7.25-7.19 (m, 1H), 6.90-6.87 (m, 2H), 6.90-
6.87 (m, 2H), 3.79 (s, 3H), 3.41 (s, 1H), 1.50-1.44 (m, 1H), 0.86-0.82
(m, 1H), 0.74-0.71 (m, 1H), 0.61-0.55 (m, 2H); 13C NMR (CDCl3,
125 MHz) δ 159.0, 149.8, 142.7, 136.8, 136.2, 127.2, 126.9, 123.0, 113.4,
90.4, 84.6, 73.7, 55.2, 23.6, 3.0, 2.4.
3-Cyclopropyl-1,5-diphenylpenta-1,4-diyn-3-ol (1q):9c yield
86%; colorless oil; 1H NMR (CDCl3, 500 MHz) δ 7.49-7.25 (m,
10H), 2.71 (s, 1H), 1.71-1.62 (m, 1H), 0.85-0.82 (m, 2H), 0.70-0.66
(m, 2H); 13C NMR (CDCl3, 125 MHz) δ 131.9, 128.7, 128.2, 122.0, 87.6,
83.6, 66.4, 22.5, 2.7.
1-Cyclopropyl-1-(1-methylcyclohexyl)-3-phenylprop-2-yn-
1-ol (1r):9c yield 78%; light yellow oil; 1H NMR (CDCl3, 500 MHz) δ
7.40-7.25 (m, 5H), 1.91 (s, 1H), 1.77-1.60 (m, 7H), 1.58-1.39 (m,
2H), 1.33-1.25 (m, 1H), 1.16 (s, 3H), 1.14-1.09 (m, 1H), 0.68-0.56
(m, 3H), 0.47-0.41 (m, 1H); 13C NMR (CDCl3, 125 MHz) δ 131.6,
128.2, 128.1, 122.9, 88.8, 85.8, 80.3, 42.4, 32.4, 31.5, 26.3, 22.1, 22.0, 17.9,
15.7, 4.6, 0.5.
1
2-Cyclopropylbut-3-yn-2-ol (1s): yield 72%; colorless oil; H
NMR (CDCl3, 400 MHz) δ 2.36 (s, 1H), 2.28 (bs, 1H), 1.57 (s, 3H),
1.19-1.07 (m, 1H), 0.64-0.46 (m, 4H); 13C NMR (CDCl3, 100 MHz)
δ 84.9, 71.6, 69.8, 29.6, 21.6, 2.4, 1.5: IR (neat, cm-1) 3369, 1446, 1215,
921, 756, 702, 669, 518; HRMS (ESI) calcd for C7H11O 111.0810,
found 111.0809
Diphenyl(2-phenylcyclopropyl)methanol (1t): yield 82%;
1
colorless oil; H NMR (CDCl3, 400 MHz) δ 7.29-7.00 (m, 13H),
6.93 (d, 2H, J = 7.7 Hz), 1.97-1.92 (m, 2H), 1.76-1.71 (m, 1H), 1.11-
1.06 (m, 1H), 0.90-0.86 (m, 1H); 13C NMR (CDCl3, 100 MHz) δ 147.4,
147.0, 142.6, 128.5, 128.27, 128.20, 127.4, 127.2, 126.7, 126.2, 125.7, 77.4,
33.5, 20.4, 12.0; IR (neat, cm-1) 3437, 3018, 1643, 1215, 772, 700, 636;
HRMS (ESI) calcd for C22H21O 301.1592, found 301.1601.
(2-Pentylcyclopropyl)diphenylmethanol (1u): yield 78%;
1
colorless oil; H NMR (CDCl3, 400 MHz) δ 7.44-7.39 (m, 4H),
Cyclopropyl(naphthalen-1-yl)(phenyl)methanol (1l): yield
1
7.31-7.21 (m, 6H), 1.86 (s, 1H), 1.40-1.20 (m, 9H), 0.85-0.81 (m,
4H), 0.66-0.62 (m, 1H), 0.40-0.36 (m, 1H); 13C NMR (CDCl3, 100
MHz) δ 147.5, 147.3, 127.9, 127.8, 127.0, 126.9, 126.8, 126.6, 77.2, 33.7,
31.6, 29.4, 29.0, 22.6, 15.2, 14.0, 9.1; IR (neat, cm-1) 3437, 3018, 2399,
1639, 1215, 927, 771, 669; HRMS (ESI) calcd for C21H27O 295.2062,
found 295.2061.
1,3-Diphenyl-1-(2-(thiophen-2-yl)cyclopropyl)prop-2-yn-
1-ol (1v):9c yield 83%; light brown oil; 1H NMR (CDCl3, 400 MHz) δ
7.80-7.78 (m, 2H), 7.51-7.33 (m, 8H), 7.05-6.71 (m, 3H), 2.66 (s,
1H), 2.52-2.48 (m, 1H), 1.83-1.78 (m, 1H), 1.62-1.57 (m, 1H),
1.16-1.09 (m, 1H); 13C NMR (CDCl3, 100 MHz) δ 146.1, 144.3,
131.9, 128.8, 128.46, 128.43, 128.0, 126.8, 125.4, 123.3, 122.7, 122.2,
89.1, 86.6, 73.7, 35.0, 16.6, 13.2.
Cyclopropyl(phenyl)methanol (1w): yield 83%; colorless oil;
1H NMR (CDCl3, 400 MHz) δ 7.42-7.27 (m, 5H), 3.97 (d, 1H, J = 8.2
Hz), 2.77 (s, 1H), 1.23-1.15 (m, 1H), 0.65-0.48 (m, 4H); 13C NMR
(CDCl3, 100 MHz) δ 144.0, 128.3, 127.4, 126.1, 78.4, 19.1, 3.7, 2.8; IR
(neat, cm-1) 3435, 3014,1633, 1492, 1452, 1215, 1026, 921, 769, 669;
HRMS (ESI) calcd for C10H13O 149.0966, found 149.0968.
1-Cyclopropylhexan-1-ol (1x): yield 79%; colorless oil; 1H
NMR (CDCl3, 400 MHz) δ 2.86-2.81 (m, 1H), 1.61-1.55 (m, 3H),
1.46-1.24 (m, 6H), 0.91-0.85 (m, 4H), 0.52-0.45 (m, 2H), 0.27-
0.18 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ 76.9, 37.2, 31.9, 25.4,
22.6, 18.0, 14.0, 2.7, 2.4; IR (neat, cm-1) 3352, 1449, 1215, 914, 757,
667, 519; HRMS (ESI) calcd for C9H19O 143.1436, found 143.1442.
70%; white solid; mp 111-113 °C; H NMR (CDCl3, 400 MHz) δ
7.29 (d, 1H, J = 7.0 Hz), 8.01 (d, 1H, J = 8.6 Hz), 7.89 (t, 2H, J = 8.9 Hz),
7.61-7.23 (m, 8H), 2.23 (s, 1H), 1.80-1.77 (m, 1H), 0.80-0.50 (m,
4H); 13C NMR (CDCl3, 100 MHz) δ 146.9, 142.1, 135.0, 131.0, 129.1,
128.8, 128.0, 127.4, 126.7, 126.1, 125.4, 125.3, 125.2, 124.7, 77.7, 23.2, 2.3,
2.2; IR (neat, cm-1) 3435, 3018, 1639, 1215, 758, 669, 499; HRMS (ESI)
calcd for C20H19O 275.1436, found 275.1435.
1-Cyclopropyl-1-phenylhexan-1-ol (1m): yield 76%; color-
less oil; 1H NMR (CDCl3, 400 MHz) δ 7.38-7.12 (m, 5H), 1.89-1.63
(m, 2H), 1.44 (s, 1H), 1.21-1.03 (m, 7H), 0.76-0.73 (m, 3H), 0.39 (q,
2H, J = 7.0 Hz), 0.30-0.17 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ
146.5, 128.1, 127.9, 126.5, 125.5, 75.0, 42.3, 32.3, 23.3, 22.5, 21.8, 14.0,
1.4, 0.7; IR (neat, cm-1) 3369, 3012, 2933, 2870, 2399, 1645, 1446,
1215, 1029, 914, 752, 702, 667, 518; HRMS (ESI) calcd for C15H23O
219.1749, found 219.1753.
1-Cyclopropyl-2,2-dimethyl-1-phenylpropan-1-ol (1n): yield
1
72%; light brown oil; H NMR (CDCl3, 400 MHz) δ 7.51-7.20 (m,
5H), 1.71-1.67 (m, 1H), 1.25 (s, 1H), 0.98 (s, 9H), 0.82-0.72 (m, 1H),
0.65-0.58 (m, 1H), 0.38-0.31 (m, 1H), 0.11--0.04 (m, 1H); 13C NMR
(CDCl3, 100 MHz) δ 146.0, 127.5, 126.8, 126.2, 78.2, 39.3, 26.0, 16.4, 4.1,
0.3; IR (neat, cm-1) 2976, 1481, 1215, 1145, 773, 704, 667, 470; HRMS
(ESI) calcd for C14H21O 205.1592, found 205.1600.
1-(4-Chlorophenyl)-1-cyclopropyl-3-(thiophen-2-yl)prop-2-
yn-1-ol (1o):9c yield 65%; pale yellow oil; 1H NMR (CDCl3, 500 MHz)
δ7.66-7.63 (m, 2H), 7.459-7.451 (m, 1H), 7.35-7.26 (m, 3H), 7.10-
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dx.doi.org/10.1021/jo102374z |J. Org. Chem. 2011, 76, 2521–2531