Tertiary acetylenic alcohols and diols on the basis of phenylacetylene and 2-methyl-3-butyn-2-ol

Article abstract of DOI:10.1023/A:1021691426904

A procedure has been proposed for the synthesis of tertiary acetylenic alcohols and diols by treatment of phenylacetylene or 2-methyl-3-butyn-2-ol with butyllithium and subsequent reaction of lithium phenylacetylide or lithium 4-lithio-2-methyl-3-butyn-2-

Full text of DOI:10.1023/A:1021691426904

Russian Journal of Organic Chemistry, Vol. 38, No. 9, 2002, pp. 1260 1265. Translated from Zhurnal Organicheskoi Khimii, Vol. 38, No. 9, 2002,
pp. 1316 1320.
Original Russian Text Copyright
2002 by Potkin, Dikusar, Kozlov.
Tertiary Acetylenic Alcohols and Diols
on the Basis of Phenylacetylene and 2-Methyl-3-butyn-2-ol*
V. I. Potkin, E. A. Dikusar, and N. G. Kozlov
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus,
ul. Surganova 13, Minsk, 220072 Belarus
e-mail: potkin@ifoch.bas-net.by
Received June 22, 2001
Abstract A procedure has been proposed for the synthesis of tertiary acetylenic alcohols and diols by treat-
ment of phenylacetylene or 2-methyl-3-butyn-2-ol with butyllithium and subsequent reaction of lithium
phenylacetylide or lithium 4-lithio-2-methyl-3-butyn-2-olate thus obtained with alicyclic, aromatic, and
terpene ketones.
We previously [1, 2] described the synthesis of
acetylenic alcohols by addition of 1-octynyl- and
1-octadecynyllithium to various ketones. Acetylenic
alcohols and diols attract interest as potential bio-
logically active substances [3]; acetylenic diols are
also promising synthons for studying their transforma-
tions under conditions of the Ritter reaction [4 6].
The IR spectra of the products contain absorption
bands at 3225 3600 (O H) and 995 1085 cm
1
(C OH). The triple carbon carbon bond gives rise
1
to a weak band in the region 2220 2245 cm .
1
In the H NMR spectra of the prepared tertiary
alcohols and diols we observed signals typical of the
corresponding initial compounds and also broadened
singlets from the hydroxy proton at 1.85 3.08 ppm.
In the spectra of carvone, isocamphanone, camphor,
and fenchone derivatives IX, XI, XIII, and XV the
OH signal is overlapped by signals from alicyclic
protons. Signals from the methyl protons in the exo
and endo positions of compounds XI, XIII, and XV
were assigned on the basis of published data [4] for
initial ketones X, XII, and XIV, taking into account
that reactions with organolithium reagents occur only
at the carbonyl group, so that the configuration of
the other molecular fragments remains unchanged.
The upfield signal was assigned to the endo-methyl
group, and the downfield signal, to the exo-oriented
methyl group.
According to the data of spectral methods and TLC
analysis, tertiary acetylenic alcohols and diols based
on terpene ketones VIIIa, VIIIb, X, XII, and XIV
are formed as a single isomer. Taking into account
the results of our previous detailed spectral studies
of related compounds [7, 8], these products were
assigned structures with endo- (XI) and exo-orienta-
tion of the hydroxy group (IXa, IXb, XIII, XV) (see
Scheme 1).
The goal of the present work was to develop
a procedure for preparation of tertiary alcohols and
diols containing an alicyclic or aromatic moiety and
an aliphatic chain having a triple C C bond in the
-position with respect to the hydroxy group. We
have found that treatment of phenylacetylene (Ia)
or 2-methyl-3-butyn-2-ol (IIa) with 1 or 2 equiv of
butyllithium, respectively, and subsequent reaction of
lithium phenylacetylide (Ib) or lithium 4-lithio-2-
methyl-3-butyn-2-olate (IIb) with alicycic (IIIa IIId)
and aromatic ketones (VIa VIe), (R)-( )- and (S)-(+)-
carvone (VIIIa, VIIIb), isocamphanone (X), ( )-cam-
phor (XII), (1S)-(+)-fenchone (XIV), and 2-adaman-
tanone (XVI) lead to formation of the corresponding
tertiary acetylenic alcohols IVa IVd, VIIa VIIe,
IXa, IXb, XVa, and XVIIa and diols Va Vd, XI,
XIII, XVb, and XVIIb (Scheme 1). The products
were isolated in 63 88% yield. Their yields, physical
constants, and analytical data are given in Table 1,
1H NMR spectra, in Table 2, and IR and UV spectra,
in Table 3.
____________
*
This study was financially supported by the Byelorussian
Tertiary acetylenic alcohols derived from natural
optically active ketones, carvone (VIIIa/VIIIb) and
Republican Foundation for Basic Research (project no. X-00-
045).
1070-4280/02/3809-1260$27.00 2002 MAIK Nauka/Interperiodica

TERTIARY ACETYLENIC ALCOHOLS AND DIOLS
1261
Scheme 1.
III V, n = 1 (a), 2 (b), 3 (c), 8 (d); IV, R = Ph; V, R = HOCMe2; VI, VII, R = Me, R = Ph (a), 1-naphthyl (b), 2-naphthyl (c);
R = Ph, R = 4-MeOC6H4 (d); R = R = 4-Me2NC6H4 (e).
XV, XVII, R = Ph (a), HOCMe2 (b).
fenchone (XIV), are also optically active compounds,
[ ]2D0, deg: 335 (IXa), +347 (IXb), 24 (XVa),
8 (XVb).
internal reference. The UV spectra were measured on
3
a Specord UV-Vis spectrophotometer from 1 10
M
solutions of Va Vd, XI, XIII, XVb, and XVIIb,
4
1 10 M solutions of IVa IVd, VIIa, VIId, IXa,
5
EXPERIMENTAL
IXb, XVa, and XVIIa, and 1 10 M solutions of
VIIb, VIIc, and VIIe in methanol. The optical rota-
tions of compounds IXa, IXb, XVa, and XVb were
measured on a SM-2 polarimeter from 3.5% solutions
in methanol. The molecular weights were determined
by cryoscopy in benzene. Neutral aluminum oxide,
L 40/250 m, Brockmann activity grade II, was used
for column chromatography. Butyllithium was pre-
pared by the procedure described in [9].
The IR spectra were recorded on a Specord 75IR
spectrometer from samples prepared as thin films
(compounds IVa, Vc, VIIa, VIIc, IXa, IXb, XI,
XIII, XVa, and XVIIa) or KBr pellets (IVb IVd,
Va, Vb, Vd, VIIb, VIId, VIIe, XVb, and XVIIb).
1
The H NMR spectra were obtained on a Tesla BS-
567A instrument in CDCl3 using tetramethylsilane as
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 38 No. 9 2002

1262
POTKIN et al.
Table 1. Yields, physical constants, and elemental analyses of compounds IVa IVd, Va Vd, VIIa VIIe, IXa, IXb, XI,
XIII, XVa, XVb, XVIIa, and XVIIb
bp,
(p, mm),
or mp,
C
Found, %
Calculated, %
M
Comp.
no.
Yield,
%
20
d
n2D0
Formula
20
C
C
H
C
H
found calcd.
IVa
75
100 101
(5 10 )
1.0681 1.5790 84.07
7.84 C13H14O
83.83
7.58
176
186.3
2
IVb
IVc
IVd
Va
Vb
Vc
80
80
73
53
69
85
54 55
41 42
88 89
84.18
84.25
8.30 C14H16O
8.64 C15H18O
83.96
84.07
84.45
71.39
72.49
8.05
8.47
9.92
9.59
9.95
198
209
274
163
177
190
200.3
214.3
284.4
168.2
182.3
196.3
84.91 10.32 C20H28O
71.68 9.84 C10H16O2
72.81 10.11 C11H18O2
73.58 10.33 C12H20O2
57 58
102 103
122 123
73.43 10.27
2
(5 10 )
Vd
VIIa
82
78
110 111
130 131
(5 10 )
77.03 11.51 C17H30O2
73.58 10.33 C12H20O2
76.64 11.35
73.43 10.27
252
190
266.4
196.3
1.1130
2
VIIb
VIIc
VIId
VIIea
IXa
74
71
71
65
77
69 70
88.31
88.39
84.18
81.17
6.28 C20H16O
6.11 C20H16O
5.84 C22H18O
7.27 C25H26N2O2 81.05
8.13 C18H20O
88.20
88.20
84.05
5.92
5.92
5.77
7.07
7.99
265
262
304
360
244
272.3
272.3
314.4
370.5
252.4
90 91
166 167
133 134
1.1525 1.5740 85.91
85.67
2
(5 10 )
IXb
XI
74
86
81
74
123 124
(5 10 )
1.1318 1.5755 85.94
8.08 C18H20O
85.67
7.99
243
226
226
244
252.4
236.4
236.4
254.4
2
125 126
76.61 10.44 C15H24O2
76.23 10.23
76.23 10.23
2
(5 10 )
XIII
XVa
107 108
0.9930 1.5025 76.38 10.25 C15H24O2
2
(5 10 )
111 112
1.9749 1.5620 85.35
8.91 C18H22O
84.99
8.82
2
(5 10 )
XVb
XVIIa
71
88
88 89
76.44 10.31 C15H24O2
85.91 8.16 C18H20O
76.23 10.23
233
246
236.4
252.4
144 145
85.67
76.88
7.99
9.46
2
(5 10 )
XVIIb
83
148 149
76.84 10.01 C15H22O2
229
234.3
a
Found N, %: 7.54. Calculated N, %: 7.56.
Table 2. 1H NMR spectra of compounds IVa IVd, Va Vd, VIIa VIIe, IXa, IXb, XI, XIII, XVa, XVb, XVIIa,
and XVIIb
Comp.
no.
Chemical shifts , ppm
IVa
IVb
IVc
IVd
Va
1.55 3.10 m [8H, (CH2)4], 2.34 br.s (1H, OH), 7.15 7.60 m (5H, Ph)
1.00 2.20 m [10H, (CH2)5], 2.40 br.s (1H, OH), 7.15 7.47 m (5H, Ph)
1.10 2.55 m [12H, (CH2)6], 2.30 br.s (1H, OH),7.12 7.50 m (5H, Ph)
1.10 1.95 m [22H, (CH2)11], 2.00 br.s (1H, OH), 7.15 7.52 m (5H, Ph)
1.53 s (6H, Me2C), 1.51 2.20 m [8H, (CH2)4], 2.59 br.s (2H, 2OH)
0.90 2.50 m [10H, (CH2)5], 1.54 s (6H, Me2C), 3.08 br.s (2H, 2OH)
Vb
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 38 No. 9 2002

TERTIARY ACETYLENIC ALCOHOLS AND DIOLS
Chemical shifts , ppm
1263
Table 2. (Contd.)
Comp.
no.
Vc
1.40 2.20 m [12H, (CH2)6], 1.52 s (6H, Me2C), 3.00 br.s (2H, 2OH)
1.20 1.95 m [22H, (CH2)11], 1.51 s (6H, Me2C), 2.17 s and 2.44 br.s (2H, 2OH)
1.86 s (3H, Me), 2.59 br.s (1H, OH), 7.15 7.78 m (10H, 2Ph)
Vd
VIIa
VIIb
VIIc
VIId
VIIe
IXa
2.13 s (3H, Me), 2.75 br.s (1H, OH), 7.15 8.95 m (12H, C10H7, Ph)
1.94 s (3H, Me), 2.69 br.s (1H, OH), 7.15 8.22 m (12H, C10H7, Ph)
2.94 br.s (1H, OH), 3.75 s (3H, MeO), 6.70 7.75 m (14H, C6H4, 2Ph)
2.78 br.s (1H, OH), 2.92 s (12H, 2Me2N), 6.57 6.80 m, 7.17 7.65 m (13H, 2C6H4, Ph)
1.16 1.85 m (6H, OH, CH, 2CH2), 1.78 s and 1.91 s (6H, 2Me), 4.70 4.85 m (2H, CH2), 5.40 5.75 m
(1H, CH), 7.15 7.45 s (5H, Ph)
IXb
XI
1.60 1.85 m (6H, OH, CH, 2CH2), 1.78 s and 1.92 s (6H, 2Me), 4.62 4.80 m (2H, CH2), 5.40 5.80 m
(1H, CH), 7.12 7.45 m (5H, Ph)
0.85 d (3H, 6-CH3, J = 7.0 Hz), 0.90 s (3H, endo-5-CH3), 1.02 s (3H, exo-5-CH3), 1.50 s (6H, Me2CC C),
1.55 2.35 m (9H, 2OH, 3CH, 2CH2)
XIII
XVa
XVb
0.86 s (3H, 1-CH3), 0.94 s (3H, endo-7-CH3), 1.06 s (3H, exo-7-CH3), 1.10 2.40 m (9H, 2OH, CH,
3CH2), 1.52 s (6H, Me2C)
1.01 s (3H, 1-CH3), 1.10 2.20 m [8H, OH, CH, CH2, (CH2)2], 1.22 s (3H, endo-3-CH3), 1.27 s (3H,
exo-3-CH3), 7.15 7.45 m (5H, Ph)
0.96 s (3H, 1-CH3), 1.12 s (3H, endo-3-CH3), 1.17 s (3H, exo-3-CH3), 1.20 2.00 m [6H, CH2, (CH2)2],
1.52 s (6H, Me2C), 1.73 br.s and 2.17 br.s (2H, 2OH)
XVIIa
XVIIb
1.35 2.15 m (14H, Ad), 2.08 br.s (1H, OH), 7.15 7.45 m (5H, Ph)
1.34 2.15 m [14H, Ad], 1.51 s (6H, Me2C), 2.03 br.s (2H, 2OH)
Table 3. IR and UV spectra of compounds IVa IVd, Va Vd, VIIa VIIe, IXa, IXb, XI, XIII, XVa, XVb, XVIIa,
and XVIIb
Comp.
no.
UV spectrum,
max, nm ( )
1
IR spectrum, , cm
IVa
3360 (OH); 3080, 3055, 3030 (CHarom); 2960, 2870 (CHaliph); 2220 (C C); 1595, 1570,
1480 (Ar); 1440 (CH2); 995 (C OH); 755, 690 (CHarom
204 (21000),
241 (20000),
252 (18000)
)
IVb
3225 (OH); 3080, 3055, 3020 (CHarom); 2930, 2855 (CHaliph); 2240 (C C); 1595, 1565,
1480 (Ar); 1445 (CH2); 1070 (C OH); 755, 690 (CHarom
205 (20000),
241 (20000),
252 (18000)
)
IVc
IVd
(CHaliph);3370 (OH); 3080, 3055, 3030, 3020 (CHarom); 2925, 2855 (CHaliph); 2225
(C C), 1595, 1570, 1480 (Ar); 1450, 1440 (CH2); 1020 (C OH); 750, 690 (CHarom
3325 (OH); 3100, 3075 3060, 3045, 3030, 3020 (CHarom); 2940, 2910, 2860, 2845
(CHaliph); 2225 (C C); 1600, 1575, 1490 (Ar); 1470, 1445 (CH2); 1060 (C OH);
251 (20000)
)
206 (24000),
241 (22000),
251 (20000)
755, 695 (CHarom
)
Va
Vb
Vc
Vd
3275 (OH); 2980, 2940, 2870 (CHaliph); 2240 (C C); 1460 (CH2); 1170, 995 (C OH)
3350 (OH); 2980, 2855 (CHaliph); 2230 (C C); 1450 (CH2); 1180, 1070 (C OH)
3340 (OH); 2975, 2930, 2855 (CHaliph); 2230 (C C); 1455 (CH2); 1170, 1025 (C OH)
3320 (OH); 2935, 2855, 2845 (CHaliph); 2230 (C C); 1470 (CH2); 1160, 1005 (C OH)
203 (150)
203 (150)
203 (200)
202 (200)
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 38 No. 9 2002

1264
POTKIN et al.
Table 3. (Contd.)
Comp.
no.
UV spectrum,
max, nm ( )
1
IR spectrum, , cm
VIIa
VIIb
VIIc
VIId
VIIe
IXa
3540, 3370 (OH); 3080, 3055, 3030 (CHarom); 2985, 2930, 2860 (CHaliph); 2230 (C C),
1595, 1570, 1485, 1445 (Ar); 1085 (C OH); 755, 700, 685 (CHarom
3600, 3390 (OH); 3080, 3055, 3025 (CHarom); 2985, 2930, 2870 (CHaliph); 2230 (C C);
1595, 1520, 1505, 1480, 1440 (Ar); 1025 (C OH); 800, 775, 755, 690 (CHarom
3590, 3370 (OH); 3080, 3055, 3020 (CHarom); 2980, 2930, 2855 (CHaliph); 2230 (C C);
1595, 1500, 1485, 1440 (Ar); 1075 (C OH); 810, 755, 690 (CHarom
3500 (OH); 3080, 3065, 3040, 3010 (CHarom); 2960, 2940, 2840 (CHaliph); 2230 (C C);
1605, 1585, 1505, 1490 (Ar); 1025 (C OH); 835, 755, 745, 695 (CHarom
3425 (OH), 3100, 3080, 3030 (CHarom); 2980, 2960, 2880, 2840 (CHaliph); 2230 (C C),
1605, 1590, 1520, 1505 (Ar); 1050 (C OH); 840, 820, 805, 790, 755, 690 (CHarom
252 (17000)
)
241 (30000),
252 (28000)
241 (31000),
252 (28000)
242 (25000),
252 (20000)
205 (66000),
252 (34000)
254 (13000)
)
)
)
)
3355 (OH); 3080, 3020 (=C H); 3080, 3055, 3030 (CHarom); 2965, 2945, 2915, 2880,
2850, 2835 (CHaliph); 2220 (C C); 1645 (C C); 1595, 1570, 1480 (Ar); 1440 (CH2);
1025 (C OH); 755, 690 (CHarom
)
IXb
3350 (OH); 3080, 3020 (=C H); 3060, 3030 (CHarom); 2965, 2945, 2915, 2880, 2855,
2835 (CHaliph); 2220 (C C); 1640 (C=C); 1595, 1560, 1485 (Ar); 1440 (CH2); 1030
205 (20000),
242 (15000),
253 (14000)
204 (200)
(C OH); 755, 690 (CHarom
)
XI
3390 (OH); 2980, 2960, 2945, 2875 (CHaliph); 2240 (C C); 1475, 1450 (CH2); 1155,
1045 (C OH)
XIII
XVa
3400 (OH); 3025, 2955, 2940, 2875 (CHaliph); 2235 (C C); 1470 (CH2); 1150, 1055
(C OH)
3475 (OH); 3080, 3055, 3030, 3020 (CHarom); 2995, 2960, 2925, 2870 (CHarom); 2220
203 (400),
237 (450)
205 (26000),
243 (24000),
252 (20000)
204 (200)
(C C); 1595, 1565, 1490 (Ar); 1055 (C OH); 755, 690 (CHarom
)
XVb
3350 (OH); 2975, 2955, 2930, 2875 (CHaliph); 2240 (C C); 1470, 1450 (CH2); 1160,
1045 (C OH)
XVIIa
3450 (OH); 3080, 3055, 3025 (CHarom); 2990, 2930, 2900, 2850 (CHaliph); 2225 (C C);
206 (23000),
241 (21000),
252 (18000)
204 (150)
1595, 1570, 1485 (Ar); 1450 (CH2); 1075 (C OH); 755, 690 (CHarom
)
XVIIb
3240 (OH); 2975, 2900, 2850 (CHaliph); 2245 (C C); 1445 (CH2); 1150, 1080 (C OH)
1-Hydroxy-1-(2-phenylethynyl)- and 1-hydroxy-
endo-2-(3-hydroxy-3-methyl-1-butynyl)-1,3,3-tri-
methylbicyclo[2.2.1]heptan-exo-2-ol (XVb), 2-hy-
droxy-2-(2-phenylethynyl)adamantane (XVIIa),
and 2-hydroxy-2-(3-hydroxy-3-methyl-1-butynyl)-
adamantane (XVIIb) (general procedure). A solu-
tion of 0.03 mol or 0.07 mol of butyllithium in hexane
was added under argon over a period of 0.5 h to
a solution of 0.035 mol of phenylacetylene (Ia) in
50 ml of anhydrous tetrahydrofuran or of 0.035 mol
of anhydrous 2-methyl-3-butyn-2-ol (IIa) in 100 ml
of tetrahydrofuran, respectively, which was vigorously
stirred at 40 to 20 C. The mixture was stirred for
1 h, 0.025 mol of ketone IIIa IIId, VIa VIe, VIIIa,
VIIIb, X, XII, XIV, or XVI was added, and the
mixture was allowed to warm up to 20 23 C over
a period of 1 2 h, stirred for 3 4 h at that temperature,
1-(3-hydroxy-3-methyl-1-butynyl)cycloalkanes IVa
IVd and Va Vd, 2,4-diphenyl-3-butyn-2-ol (VIIa),
2-(1-naphthyl)-4-phenyl-3-butyn-2-ol (VIIb), 2-(2-
naphthyl)-4-phenyl-3-butyn-2-ol (VIIc), 1-(4-
methoxyphenyl)-3-phenyl-2-propyn-1-ol (VIId),
1,1-bis(4-dimethylaminophenyl)-3-phenyl-2-pro-
pyn-1-ol (VIIe), (5R)-( )-5-isopropenyl-2-methyl-
1-(2-phenylethynyl)-2-cyclohexenol (IXa), (5S)-(+)-
5-isopropenyl-2-methyl-1-(2-phenylethynyl)-2-cy-
clohexenol (IXb), exo-2-(3-hydroxy-3-methyl-1-
butynyl)-5,5,6-trimethylbicyclo[2.2.1]heptan-endo-
2-ol (XI), ( )-endo-2-(3-hydroxy-3-methyl-1-
butynyl)-1,7,7-trimethylbicyclo[2.2.1]heptan-exo-ol
(XIII), (1S)-( )-endo-2-(2-phenylethynyl)-1,3,3-tri-
methylbicyclo[2.2.1]heptan-exo-2-ol (XVa), (1S)-( )-
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 38 No. 9 2002

TERTIARY ACETYLENIC ALCOHOLS AND DIOLS
1265
and was left to stand for 18 h. The resulting lithium
or dilithium alkoxide was hydrolyzed with 300 ml of
water, the product was extracted into diethyl ether,
the extract was washed with water, dried over CaCl2,
and evaporated, and the residue was kept in a vacuum.
Compounds IVa, Vc, VIIa, IXa, IXb, XI, XIII,
XVa, and XVIIa were purified by vacuum distilla-
tion, compounds IVb IVd, Va, Vb, Vd, VIId, VIIe,
XVb, and XVIIb were recrystallized from hexane,
and compounds VIIb and VIIc were subjected to
molecular distillation [10] with subsequent recrystal-
lization from hexane (VIIb). Compounds Vc, VIIc,
XI, and XVIIa are colorless viscous glassy liquids.
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