PAPER
Solid-Support-Bound 1-Aminoimidazolium Chlorochromate
387
evaporated to dryness. The residue was chromatographed on silica Acknowledgement
gel using hexanes/EtOAc (9:1) as eluent. Compound 14 (0.51 g,
We thank the Dirección General de Enseñanza Superior (DGES,
project PM97-0074) and the University of Alcalá (019/96; E032/
8
8%) was obtained as a yellowish oil.
1
H NMR (CDCl , 200 MHz): = 7.53 (d, J = 7.8 Hz, 1 H), 7.32 (t,
3
9
7) for financial support.
J = 7.8 Hz, 1 H), 7.15 (d, J = 12.4 Hz, 1 H), 6.93 (t, J = 7.8 Hz, 1
H), 6.85 (d, J = 7.8 Hz, 1 H), 5.95 (d, J = 12.4 Hz, 1 H), 4.15 (q,
J = 6.9 Hz, 2 H), 3.80 (s, 3 H), 1.30 (t, J = 6.9 Hz, 3 H).
References
1
3
C NMR (CDCl , 62 MHz): = 166.3, 157.0, 138.9, 130.6, 130.2,
3
(
1) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C.
1
24.0, 119.9, 119.8, 60.0, 55.3, 14.0
Tetrahedron 1997, 53, 5643.
MS (EI): m/z (%) = 206 (44, M+).
(2) Obrecht, D.; Villalgordo, J. M. In Solid-Supported
Combinatorial and Parallel Synthesis of Small-Molecular-
Weight Compound Libraries; Baldwin, J. E.; Williams, R. M.,
Eds.; Tetrahedron Organic Chemistry Series Vol. 17;
Pergamon, Elsevier Science: Oxford, 1998.
Anal. calcd. for C H O : C, 69.89; H, 6.84. Found: C: 69.54; H,
7
12
14
3
.23.
IR (CHCl ): = 2937, 2840, 1720, 1629, 1599, 1577, 1487, 1437,
1
3
1
185, 1159, 1110 cm .
(
3) Bunin, B. A. In The Combinatorial Index; Academic Press:
London, 1998.
cis-3-(2-Methoxyphenyl)prop-2-en-1-ol (11l)
Compound 14 (0.25 g, 1.21 mmol) was dissolved in THF (4 mL)
under argon, cooled to 0 ºC and 1 M DIBAH in hexane (2.42 mL,
(4) Cardillo, G.; Orena, M.; Sandri, S. Tetrahedron Lett. 1976, 17,
3985.
(5) Brunelet, T.; Jouitteau, C.; Gelbard, G. J. Org. Chem. 1986,
51, 4016.
2
.42 mmol) was added. The mixture was stirred at r.t. for 20 h, the
reaction quenched with aq sat sodium tartrate solution (50 mL) and
(6) Cainelli, G.; Cardillo, G.; Orena, M.; Sandri, M. J. Am. Chem.
Soc. 1976, 98, 6737.
the mixture extracted with CH Cl (3 î 20 mL). The combined or-
2
2
ganic extracts were dried (MgSO ) and the solvent was evaporated.
The residue was chromatographed on silica gel using hexanes/
EtOAc (9:1 to 7:3) to give 11l (0.11 g, 55%) as a colourless oil.
(7) Wade Jr., L. G.; Stell, L. M. J. Chem. Educ. 1980, 57, 438.
(8) Fréchet, J. M. J.; Warnock, J.; Farrall, M. J. J. Org. Chem.
1978, 43, 2618.
4
1
(9) Fréchet, J. M. J.; Darling, P.; Farrall, M. J. J. Org. Chem.
H NMR (CDCl , 300 MHz): = 7.26 (dt, J = 7.7 Hz, J = 1.6 Hz, 1
3
1981, 46, 1728.
H), 7.10 (dd, J = 7.7 Hz, J = 1.6 Hz, 1 H), 6.93 (t, J = 7.7 Hz, 1 H),
6
J = 11.3 Hz, J = 6.8 Hz, 1 H), 4.31 (dd, J = 6.8 Hz, J = 1.2 Hz, 2 H),
3
(
(
10) Canielli, G.; Contento, M.; Manescalchi, F.; Plessi, L.
Synthesis 1989, 45.
11) Harrison, C. R.; Hodge, P. J. Chem. Soc., Perkin Trans. 1
.88 (d, J = 7.7 Hz, 1 H), 6.68 (d, J = 11.3 Hz, 1 H), 5.92 (dt,
.83 (s, 3 H), 1.95 (s, 1 H).
1
982, 509.
(12) Bessodes, M.; Antonakis, K. Tetrahedron Lett. 1985, 26,
305.
(13) Hinzen, B.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997,
907.
1
3
C NMR (CDCl , 75 MHz): = 156.8, 130.9, 130.2, 128.7, 126.7,
3
1
25.3, 120.1, 110.4, 59.8, 55.4
1
MS (EI): m/z (%) = 164 (59, M+).
1
Anal. calcd. for C H O : C, 73.15; H, 7.37. Found: C, 72.83; H,
7
10
12
2
(
(
14) Hinzen, B.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1998, 1.
15) Harrison, C. R.; Hodge, P. J. Chem. Soc., Chem. Commun.
1974, 1009.
.55.
IR (CHCl ): = 3340, 2934, 1597, 1487, 1461, 1435, 1245, 1109,
1
3
1
022, 754 cm .
(16) Cheng, Y.-S.; Liu, W.-L.; Chen, S.-H. Synthesis 1980, 223.
(17) Herscovici, J.; Egron, M.-J.; Antonakis, K. J. Chem., Soc.
3
-(4-Hydroxymethylphenoxy)propan-1-ol (11n)
Perkin Trans. 1 1982, 1967.
To a solution of 15 (0.5 g, 4 mmol) in MeCN (2.5 mL) was added
powdered KOH (0.25g, 4.4 mmol) and the mixture was stirred for
(18) Parlow, J. J. Tetrahedron Lett. 1995, 36, 1395.
(19) Tamani, B.; Hatam, M.; Mohadjer, D. Polymer 1991, 32,
2662.
3
0 min at r.t. 3-Bromopropanol (0.54 mL, 6 mmol) was added and
the mixture stirred for a further 16 h at r.t. The mixture was filtered
and the filtrate evaporated to dryness. The residue was chromato-
graphed on silica gel using hexanes/EtOAc (1:1) as eluent to give
(20) Tamani, B.; Goudarzian, N. Eur. Polym. J. 1992, 28, 1035.
(21) Tamani, B.; Yeganeh, H. Tetrahedron 1997, 53, 7889.
(22) Wang, G.-P.; Chen, Z.-C. Synth. Commun. 1999, 29, 2859.
(23) Ley, S. V.; Thomas, A. W.; Finch, H. J. Chem. Soc., Perkin
Trans. 1 1999, 669.
1
1n (0.59 g, 81%) as a white solid (mp 77.8 78 ºC).
1
H NMR (CDCl , 300 MHz): = 7.27 (d, J = 8.5 Hz, 2 H), 6.88 (d,
3
(
24) Ley, S. V.; Schucht, O.; Thomas, A. W.; Murray, P. J. J.
Chem. Soc., Perkin Trans. 1 1999, 1251.
J = 8.5 Hz, 2 H), 4.60 (d, J = 4.4 Hz, 2 H), 4.11 (t, J = 5.8 Hz, 2 H),
3
.85 (br q, J = 5.5 Hz, 2 H), 2.04 (q, J = 5.8 Hz, 2 H), 1.90 (br t,
(25) Tohma, H.; Takizawa, S.; Maegawa, T.; Kita, Y. Angew.
Chem., Int. Ed. Engl. 2000, 39, 1306.
J = 5.1 Hz, 1 H), 1.77 (br t, J = 5.5 Hz, 1 H).
1
3
C NMR (CDCl , 62 MHz): = 133.3, 128.6, 114.5, 65.7, 64.9,
3
(26) Osa, T.; Kashiwagi, Y.; Mukai, K.; Ohsawa, A.; Bobbitt, J. M.
Chem. Lett. 1990, 75.
(27) Kashiwagi, Y.; Ohsawa, A.; Osa, T.; Ma, Z.; Bobbitt, J. M.
Chem. Lett. 1991, 581.
6
0.3, 31.9
MS (EI): m/z (%) = 182 (83, M+).
Anal. calcd. for C H O : C: 65.92; H, 7.74. Found: C: 66.30; H,
10
14
3
(
28) Kashiwagi, Y.; Yanagisawa, Y.; Kurashima, F.; Anzai, J.-I.;
Osa, T.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun.1996,
2745.
8
.09
IR (KBr): = 3248, 2922, 2868, 1612, 1514, 1468, 1248, 1020
1
cm .
(29) Yamauchi, Y.; Maeda, H.; Ohmori, H. Chem. Pharm. Bull.
997, 45, 2024.
1
(
30) Martinez, Y.; Heras, M. A.; Vaquero, J. J.; García-Navío, J.
L.; Alvarez-Builla, J. Tetrahedron Lett. 1995, 36, 8513.
31) Ning, R. Y. Chem. Eng. News 1973 (# 51), 36.
32) Taylor, E. C.; Sun, J. H. Synthesis 1980, 801.
(
(
Synthesis 2001, No. 3, 382–388 ISSN 0039-7881 © Thieme Stuttgart · New York