B. M. Choudary et al. / Tetrahedron 56 (2000) 7291–7298
7297
137.6, 133.3, 132.8, 129.9, 128.7, 122.1 (Ar carbons), 21.8,
20.7 (CH3); MS (EI) m/z 310 (Mϩ, 13) 155 (45), 127 (7), 91
(100), 65 (27).
CHOH), 4.46 (1H, m, CHOTs), 7.32 (2H, d, m-H,
J8.1 Hz), 7.79 (2H, d, o-H, J8.1 Hz).
Cyclohexyl benzenesulfonate (5).32 Thick oil; IR (film)
1
2-Hydroxypropyl p-toluenesulfonate (4a). The crude
product was purified by silica gel column in EtOAc/hexane
1:4. Mp 48–49ЊC (Lit.18 mp 49.5–50ЊC); IR (KBr) 1175,
1170, 1351 cmϪ1; H NMR (200 MHz, CDCl3) d 1.34–
1.80 (10H, m, –[CH2]5–), 4.53 (1H, m, CHO–), 7.56 (3H,
m, Ar-H), 7.91 (2H, d, J7.5 Hz, Ar-H); 13C NMR
(200 MHz, CDCl3) d 133.27, 129.13, 128.99, 127.35 (Ar
carbons), 81.81 (CHO), 32.17, 24.68, 23.18 (alkane).
1
1352 cmϪ1; H NMR (200 MHz, CDCl3) d 1.16 (3H, d,
J6.0 Hz, CH3), 2.21 (1H, brs, OH), 2.44 (3H, s, CH3),
3.82 (1H, m, CH–), 4.04 (2H, m, CH2O–), 7.32 (2H,
d, m-H, J8.1 Hz), 7.79 (2H, d, o-H, J8.1 Hz); MS
(EI) m/z 200 (MϩϪCH3, 13), 156 (34), 91 (100), 57 (48),
43 (39).
Cyclohexyl methanesulfonate (6).33 Thick oil; IR (film)
1
1175, 1354 cmϪ1; H NMR (200 MHz, CDCl3) d 1.32–
1.98 (10H, m, –[CH2]5–), 2.97 (3H, s, CH3), 4.78 (1H, m,
CHO–).
2-Hydroxy-3,3-dimethylbutyl p-toluenesulfonate (4b).
Mp 45–46ЊC (Lit.29a mp 45–46ЊC); IR (KBr) 1179, 1351,
1
3546 cmϪ1; H NMR (200 MHz, CDCl3) d 0.90 (9H, s,
Acknowledgements
–CMe3), 2.45 (3H, s, CH3), 2.64 (1H, brs, OH), 3.52 (1H,
dd, J2.3, 9.3 Hz, CH2OTs), 3.93 (1H, t, J9.3 Hz,
–CH2CH–), 4.22 (1H, dd, J2.3, 9.3 Hz, CH2OTs), 7.34
(2H, d, m-H, J8.1 Hz), 7.80 (2H, d, o-H, J8.1 Hz).
One of the authors (N. S. C.) thanks the Council of Scientific
and Industrial Research, New Delhi for the award of
research fellowship.
2-Hydroxy-3-chloropropyl p-toluenesulfonate (4c).18
Thick oil; IR (film) 1178, 1351 cmϪ1
;
1H NMR
References
(200 MHz, CDCl3) d 2.43 (3H, s, CH3), 2.65 (1H, brs,
OH), 3.56 (2H, d, J5.3 Hz, CH2Cl), 4.02 (1H, m, CH),
4.09 (2H, d, J5.0 Hz, CH2O), 7.34 (2H, d, m-H,
J8.1 Hz), 7.78 (2H, d, o-H, J8.1 Hz); MS (EI) m/z 155
(MϩϪC3H6ClO2, 65), 91 (100), 65 (28), 43 (46).
1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic
Synthesis, 3rd ed.; Wiley: New York, 1999.
2. (a) Adlington, R. M.; Barrett, A. G. M.; Quayle, P.; Walker, A.
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2-Hydroxydecyl p-toluenesulfonate (4d). Mp 39–41ЊC
(Lit.29b mp 39–41ЊC); IR (film) 1173, 1358 cmϪ1 1H
;
NMR (200 MHz, CDCl3) d 0.9 (3H, t, J6.4 Hz, CH3),
1.1–1.7 (14H, m), 2.12 (1H, brs, OH), 2.46 (3H, s, CH3),
3.70–4.02 (3H, m, –CH2CH–), 7.38 (2H, d, m-H,
J8.6 Hz), 7.81 (2H, d, o-H, J8.6 Hz).
2,3-Dihydroxypropyl p-toluenesulfonate (4e). The crude
product was purified by silica gel column in EtOAc/hexane
1:1. mp 51–53ЊC (Lit.29c mp 54ЊC); IR (KBr) 1175, 1356,
5. Hartung, J.; Hunig, S.; Kneuer, R.; Schwarz, M.; Wenner, H.
Synthesis 1997, 1433.
1
3365 cmϪ1; H NMR (200 MHz, CDCl3) d 2.40 (3H, s,
6. (a) Karaman, R.; Leader, H.; Goldblum, A.; Breuer, E. Chem.
Ind. (L) 1987, 857. (b) Klamann, D.; Weyerstahl, P. Chem. Ber.
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1985, 33, 1380. (d) Mukaiyama, T.; Hojo, K. Chem. Lett. 1976,
893.
CH3), 3.5–3.95 (5H, m, 3-H2, 2-H and 2×OH), 4.09 (2H,
d, J5.0 Hz, 1-H2), 7.38 (2H, d, m-H, J8.1 Hz), 7.8 (2H,
d, o-H, J8.1 Hz).); 13C NMR (200 MHz, CDCl3) d 145.7,
132.7, 130.5, 120.5, 71.3, 70.1, 63.3, 22.1.
7. (a) O’Connell, J. F.; Rapoport, H. J. Org. Chem. 1992, 57, 4775.
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205.
2-Hydroxyethyl p-toluenesulfonate (4f).6c Thick oil; IR
(film) 1179, 1351, 3400 cmϪ1
;
1H NMR (200 MHz,
CDCl3) d 2.44 (3H, s, CH3), 3.78 (2H, t, J5.1 Hz,
CH2OH), 4.12 (2H, t, J5.1 Hz, CH2O), 7.32 (2H, d,
m-H, J8.1 Hz), 7.79 (2H, d, o-H, J8.1 Hz); MS (EI)
m/z 216 (Mϩ, 2), 155 (33), 121 (100), 91 (73), 65 (19).
8. (a) Bennett, H. J. Chem. Soc. 1941, 656. (b) Sane, J. J. Chem.
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9. (a) Smith, J. G. Synthesis 1984, 629. (b) Oi, R.; Sharpless, K. B.
Tetrahedron Lett. 1992, 33, 2095.
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4-Hydroxybutyl p-toluenesulfonate (4g).30 Thick oil; IR
1
(film) 1187, 1351 cmϪ1; H NMR (200 MHz, CDCl3) d
1.54 (2H, m, CH2), 1.67 (2H, m, CH2), 2.44 (3H, s, CH3),
3.31 (2H, t, J6.5 Hz, CH2OH), 4.01 (2H, t, J5.8 Hz,
CH2O), 7.32 (2H, d, m-H, J8.1 Hz), 7.79 (2H, d, o-H,
J8.1 Hz).
2-Hydroxycyclooctyl p-toluenesulfonate (4h).31 Thick oil;
11. (a) Choudary, B. M.; Kumar, K. R.; Jamil, Z.; Thyagarajan, G.
J. Chem. Soc. Chem. Commun. 1985, 931. (b) Choudary, B. M.;
Bharathi, P. J. Chem. Soc. Chem. Commun. 1987, 1505.
1
IR (film) 1171, 1350 cmϪ1; H NMR (200 MHz, CDCl3) d
1.27–2.06 (12H, m, alkane), 2.43 (3H, s, CH3), 3.73 (1H, m,