1322
M. J. P. Vaismaa et al. · An Improved and Green Preparation of 3-(Alkylthio)propionic Acids
were combined, dried (Na2SO4), filtered and concentrated 6.6 Hz, 2 H, CH2O), 3.38 (s, 3 H, CH3), 2.9 – 2.6 (m, 4 H,
yielding a colorless oil (1.33 g, 7.7 mmol, 82 %). – 1H NMR SCH2CH2CO), 2.74 (t, J = 6.6 Hz, 2 H, OCH2CH2S). –
(200 MHz, CDCl3): δ = 11.42 (br. s, 1 H, OH), 2.85 – 2.6 (m, 13C NMR (50 MHz, CDCl3): δ = 177.5 (C=O), 72.0, 58.5,
6 H, CH2SCH2CH2CO), 2.53 (t, J = 7.0 Hz, 2 H, CNCH2), 34.6, 31.3, 26.9. – HRMS ((–)ESI): m/z = 163.0400 (calcd.
1.95 (m, J = 7.0 Hz, 2 H, CH2CH2CH2). – 13C NMR 163.0395 for C6H11O3S).
(50 MHz, CDCl3): δ = 177.8 (C=O), 119.1 (CN), 34.4, 30.5,
26.3, 24.9, 15.9. – HRMS ((–)ESI): m/z = 172.0420 (calcd.
Acknowledgements
172.0432 for C7H10NO2S).
The authors wish to thank Mrs. Pa¨ivi Joensuu, Mr. Petri
Reponen and Mrs. Sari Ek for their assistance in MS char-
acterization. M. V. thanks the Academy of Finland, the Jenni
and Antti Wihuri Foundation, and the Tauno To¨nning Foun-
dation for financial support.
3-(2-Methoxyethylthio)propionic acid (26)
Yield 90 % (pale yellow oil, 1.55 g, 8.5 mmol). – 1H NMR
(200 MHz, CDCl3): δ = 11.49 (br. s, 1 H, OH), 3.59 (t, J =
[1] S. Cadamuro, I. Degani, R. Fochi, V. Regondi, Synthe-
sis 1986, 12, 1070 – 1074, and references cited therein.
[2] H. Shigemoto, K. Kawamoto, JP Patent 03220310,
1991.
[8] a) Y. B. Pisarskii, T. V. Nefedova, N. M. Boiko, L. T.
Moskvitina, L. A. Mansurova, A. B. Skornyakova, T. Y.
Pushechkina, A. N. Vavilova, V. B. Kazimirovskaya,
B. A. Trofimov, Khimiko-Farmatsevticheskii Zhurnal
1991, 25, 38 – 40; Chem. Abstr. 1991, 116, 6124;
b) J. Skorve, B. Ruyter, A. C. Rustan, E. N. Chris-
tiansen, C. A. Drevon, R. K. Berge, Biochem. Pharma-
col. 1990, 40, 2005 – 2012; Chem. Abstr. 1990, 114,
40284.
[9] a) J. G. Hendrickson, L. F. Hatch, J. Org. Chem. 1960,
25, 1747 – 1752; b) M. E. Peach, The Chemistry of the
Thiol Group, Part 2, Ed.: S. Patai), John Wiley, London,
1974, pp. 721 – 784; c) S. Oae, J. T. Doi, Organic Sul-
fur Chemistry: Structure and Mechanism, CRC Press,
Boca Raton, 1991.
[10] R. M. Peck, A. P. O’Connell, H. J. Creech, J. Med.
Chem. 1966, 9, 217 – 221.
[11] L. Rapoport, A. Smith, M. S. Newman, J. Am. Chem.
Soc. 1947, 69, 693 – 694.
[12] J. T. Doi, M. H. Goodrow, W. K. Musker, J. Org. Chem.
1986, 51, 1026 – 1029.
[13] a) K. Tsutsumi, T. Yabukami, K. Fujimoto, T. Kawase,
T. Morimoto, K. Kakiuchi, Organometallics 2003,
22, 2996 – 2999; b) K. Tsutsumi, K. Fujimoto,
T. Yabukami, T. Kawase, T. Morimoto, K. Kakiuchi,
Eur. J. Org. Chem. 2004, 504 – 510.
[3] a) C. J. Easton, A. Ferrante, T. A. Robertson, L. Xia,
Aust. J. Chem. 2002, 55, 647 – 653; b) S. Nagase,
H. Ban, K. Fujimura, H. Inagaki, JP Patent 05254057,
1993; Chem. Abstr. 1993, 120, 166964; c) D. R.
Chisholm, M. H. Fisch, M. E. Flanagan, R. D. Peveler,
EP Patent 413562, 1991; Chem. Abstr. 1991, 115,
8097; d) M. E. Flanagan, M. H. Fisch, R. D. Peveler, EP
Patent 413563, 1991; Chem. Abstr. 1991, 115, 8096.
[4] a) K. Ueda, H. Ito, T. Usami, JP Patent 2000178574,
2000; Chem. Abstr. 2000, 133, 61168; b) K. Tsuruoka,
N. Sei, F. Takahashi, JP Patent 06145689, 1994; Chem.
Abstr. 1994, 121, 208958; c) K. Takeda, JP Patent
04034088, 1992; Chem. Abstr. 1992, 116, 257314.
[5] Additives for polymers: a) E. Tobita, T. Funamizu,
JP Patent 10081876, 1998; Chem. Abstr. 1998, 128,
271279; b) T. Yoshizawa, T. Tanaka, JP Patent
10273553, 1998; Chem. Abstr. 1998, 129, 276968;
c) K. Hyoshi, Y. Yamada, JP Patent 08231779, 1996;
Chem. Abstr. 1996, 125, 302474; d) M. Shimada,
H. Noda, JP Patent 09188785, 1997; Chem. Abstr.
1997, 127, 136858.
[6] Additives for resins: a) M. Minagawa, T. Haruna,
M. Takahashi, EP Patent 81235, 1983; Chem. Abstr.
1983, 99, 123614; b) Sumitomo Chemical Co., Ltd. JP
Patent 58023841, 1983; Chem. Abstr. 1983, 99, 89114;
c) Y. Nakahara, T. Haruna, US Patent 4349468, 1982;
Chem. Abstr. 1982, 97, 217442.
[14] P. P. C. Bullman, S. S. Klair, M. P. Brown, C. S. Smith,
S. J. Maginn, S. Mulley, Tetrahedron 1992, 48, 5933 –
5940.
[15] Y. Hu, Z.-C. Chen, Z.-G. Le, Q.-G. Zheng, Synth. Com-
mun. 2004, 34, 2039 – 2046.
[7] a) V. Miskiniene, N. Cenas, E. Boreko, G. Vla-
dyko, Chemija 2001, 12, 80 – 83; Chem. Abstr.
2001, 135, 242173; b) V. Miskiniene, A. Kinzirsky,
Chemija 1997, 62; Chem. Abstr. 1997, 127, 130539;
c) B. A. Trofimov, A. N. Vavilova, A. I. Mikhaleva,
G. V. Vladyko, L. V. Karobchenko, E. I. Boreko, N. P.
Mishaeva, A. A. Zgirovskaya, A. I. Azarova, Khimiko-
Farmatsevticheskii Zhurnal 1995, 29, 56 – 58; Chem.
Abstr. 1995, 124, 75515.
[16] M. Feroci, A. Inesi, L. Rossi, Synth. Commun. 1999,
29, 2611 – 2615.
[17] S. Vijaikumar, K. Pitchumani, J. Mol. Catal. A: Chem.
2004, 217, 117 – 120.
[18] A. H. Soloway, J. E. Wright, V. Subramanyam, J. J.
Gozzo, J. Med. Chem. 1977, 20, 1357 – 1362.
[19] M. J. P. Vaismaa, unpublished results. The reactions
with hexanethiol, pentanethiol and benzene thiol
were carried out for comparison and characterization
Unauthenticated
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