Please do not adjust margins
ChemComm
Page 4 of 5
DOI: 10.1039/C8CC05843A
COMMUNICATION
Journal Name
acknowledged.
kit/products/4265/electrasyn-2.0-package, (accessed 19
March 2018).
Conflicts of interest
The authors confirm the absence of conflicts of interest.
26
H. Hofer and M. Moest, Justus Liebigs Ann. Chem., 1902,
323, 284–323.
2
2
2
3
7
8
9
0
F. Lebreux, F. Buzzo and I. E. Marko, ECS Trans., 2008, 13,
1–10.
F. Lebreux, F. Buzzo and I. Markó, Synlett, 2008, 2815–
Notes and references
1
P. J. Kocienski, Protecting groups, Georg Thieme Verlag,
Stuttgart . New York, 2005.
2
820.
P. G. M. Wuts and C. Sutherland, Tetrahedron Lett., 1982,
3, 3987–3990.
2
P. G. M. Wuts, Greene’s Protective Groups in Organic
Synthesis Fifth Edition, John Wiley & Sons, Ltd, Hoboken,
NJ, Fifth., 2014.
2
Procedure: A flame dried 250 mL three-necked flask was
equipped with a magnetic stir bar and a reflux condenser.
Sodium hydride (1.20 g, 60% dispersion in mineral oil, 30
3
G. Sartori, R. Ballini, F. Bigi, G. Bosica, R. Maggi and P. Righi,
Chem. Rev., 2004, 104, 199–250.
o
mmol) was then suspended in dry THF (20 mL) at 0 C
4
5
J. P. Yardley and H. Fletcher, Synthesis (Stuttg)., 1976, 244.
A. F. Kluge, K. G. Untch and J. H. Fried, J. Am. Chem. Soc.,
under argon. Alcohol 1 (10 mmol), dissolved in dry THF (30
mL), was then added slowly. After 30 min, bromoacetic
acid 2 (10 mmol), dissolved in dry THF (30 mL), was added
dropwise. The mixture was heated to reflux, and the
progress of the reaction was monitored by TLC. Upon
completion of the reaction, as shown by TLC, the mixture
was cooled down to room temperature and diluted with
water (60 mL). The mixture was extracted with hexane (2 x
1
972, 94, 7827–7832.
B. C. Ranu, A. Majee and A. R. Das, Synth. Commun., 1995,
5, 363–367.
6
7
8
9
1
2
P. Kumar, S. V. N. Raju, R. S. Reddy and B. Pandey,
Tetrahedron Lett., 1994, 35, 1289–1290.
R. T. Drew, S. Laskin, M. Kuschner and N. Nelson, Arch.
Environ. Health, 1975, 30, 61–69.
3
0 mL), the aqueous layer was acidified with HCl (2 M) until
pH 2 was reached and extracted with diethyl ether (3 x 30
mL). The combined organic layers were dried over MgSO
K. Fuji, S. Nakano and E. Fujita, Synthesis (Stuttg)., 1975,
276–277.
4
,
0
G. A. Olah, A. Husain, B. G. Balaram Gupta and S. C.
Narang, Synthesis (Stuttg)., 1981, 471–472.
H. K. Patney, Synlett, 1992, 567–568.
the solvent was removed under reduced pressure and the
crude mixture was purified by column chromatography on
silica gel (petroleum ether / ethyl acetate) to give the pure
α-alkoxy carboxylic acids 3.
H. Horikawa, T. Iwasaki, K. Matsumoto and M. Miyoshi, J.
Org. Chem., 1978, 43, 335–337.
11
2
1
T. S. Jin, T. S. Li and Y. T. Gao, Synth. Commun., 1998, 28,
8
37–841.
B. Karimi and L. Ma’mani, Tetrahedron Lett., 2003, 44,
051–6053.
31
32
33
1
3
4
6
H. G. Thomas and E. Katzer, Tetrahedron Lett., 1974, 15,
1
M. Moghadam, S. Tangestaninejad, V. Mirkhani, I.
Mohammadpoor-Baltork, M. Khajehzadeh, F. Kosari and M.
Araghi, Polyhedron, 2010, 29, 238–243.
887–888.
H. Tanaka, M. Kuroboshi and S. Torii, in Organic
Electrochemistry, Fifth Edition, CRC Press, 2015, pp. 1267–
1
5
6
B. F. Marcune, S. Karady, U. H. Dolling and T. J. Novak, J.
Org. Chem., 1999, 64, 2446–2449.
M. Faraday, Philos. Trans. R. Soc. London, 1832, 122, 125–
1307.
34
General Electrolysis Procedure: In an undivided beaker-
type cell (100 mL) equipped with two graphite electrodes
1
162.
(
2 cm × 3 cm), or in an Electrasyn 2.0, α-alkoxy carboxylic
1
1
7
8
H. Kolbe, Justus Liebigs Ann. Chem., 1849, 69, 257–294.
D. Hayrapetyan, V. Shkepu, O. T. Seilkhanov, Z. Zhanabil
and K. Lam, Chem. Commun., 2017, 53, 8451–8454.
K. Lam and W. E. Geiger, J. Org. Chem., 2013, 78, 8020–
acid 3 (1.87 mmol) was dissolved in MeOH (50 mL). The
acid was then partially neutralised with NaOMe (0.46
-2
mmol) and a current density of 100 mA.cm was applied.
The reaction was monitored by TLC. Upon completion of
the reaction, as shown by TLC, the solvent was carefully
removed under reduced pressure and then water (10 mL)
was added (in the case the solution was not basic, 5 mL of
19
8027.
2
2
0
1
K. Lam and I. E. Markó, Chem. Commun., 2009, 95–97.
E. J. Horn, B. R. Rosen and P. S. Baran, ACS Cent. Sci., 2016,
2, 302–308.
1
M KOH were added). The aqueous mixture was then
extracted with diethylether (3 x 15 mL). The organic layers
were collected, dried over Na CO , and concentrated
22
O. Hammerich and B. Speiser, Eds., Organic
Electrochemistry: Revised and Expanded, CRC Press, 5th
edn., 2015.
2
3
under reduced pressure to yield the clean product 4
without the need for any further purifications.
F. P. Marmsäter and F. G. West, J. Am. Chem. Soc., 2001,
23
24
25
X. Ma, X. Luo, S. Dochain, C. Mathot and I. E. Markò, Org.
Lett., 2015, 17, 4690–4693.
E. J. Horn, B. R. Rosen, Y. Chen, J. Tang, K. Chen, M. D.
Eastgate and P. S. Baran, Nature, 2016, 533, 77–81.
ElectraSyn 2.0 Package - IKA,
3
5
6
1
23, 5144–5145.
M. Braun and W. Kotter, Angew. Chemie - Int. Ed., 2004,
3, 514–517.
3
4
4
| J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins