2
187
Synthesis
N. Le Marquer et al.
PSP
for 4 h, and then concentrated under reduced pressure to approxi-
mately 100 mL and cooled to 0 °C. Filtration of the resulting precipi-
tate and drying under vacuum yielded 2.22 g of compound 3. Concen-
tration of the filtrate to 20 mL and repetition of the above operation
yield a second crop of 473 mg of 3.
Acknowledgment
We wish to thank Patricia Gangnery and Emmanuelle Mebold for
HRMS measurements, Amélie Durand and Corentin Jacquemoz for
NMR analysis, and Frederic Legros for his assistance in the laboratory.
Combined yield: 2.69 g (95%); yellow solid; mp 255 °C.
IR (ATR): 3470, 3274, 3175, 2976, 1734, 1687, 1579, 1486, 1408, 1257,
Supporting Information
–1
1108, 1067, 1013, 853, 771 cm .
1H NMR (400 MHz, DMSO): δ = 1.23 (t, J = 7.2 Hz, 6 H), 1.79–2.24 (m,
Supporting information for this article is available online at
http://dx.doi.org/10.1055/s-0034-1380432.
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H), 2.64 (d, J = 18.2 Hz, 2 H), 2.87 (d, J = 18.2 Hz, 2 H), 4.17 (dq,
J = 2.8 Hz, J = 7.1 Hz, 4 H), 5.90 (br s, 4 H), 9.06 (s, 2 H).
13C NMR (100 MHz, DMSO): δ = 13.8, 26.1, 33.8, 49.0, 60.2, 149.0,
References
156.4, 170.5.
+
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found: 397.1840.
4
6
6
5
(2) Ermer, O.; Dunitz, J. D. Chem. Commun. 1968, 567.
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lid. Caution: it is important to pay attention to the volume of the cru-
cible in order to contain the generated foam. The mixture was heated
in an oil bath with stirring from r.t. to 160 °C over 45 min. Caution:
gas release is observed resulting in abundant foaming of the mixture.
7
659.
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(
(
(
1
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The resulting foam was suspended in H O and acidified to pH 1 by al-
2
ternate addition of concentrated HCl and ice. The precipitated prod-
uct was filtered off and dried under vacuum to give the desired diacid
(
(
(
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4
.
Yield: 818 mg (75%); white solid; mp 350 °C (dec.).
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IR (ATR): 2959, 2877, 2648, 2531, 1683, 1460, 1413, 1307, 1281, 1093,
–1
(10) Ritchie, C. D.; Megerle, G. H. J. Am. Chem. Soc. 1967, 89, 1452.
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961, 849, 756 cm
.
(
1H NMR (400 MHz, DMSO): δ = 1.68 (s, 12 H), 12.15 (br s, 2 H).
1
13
C NMR (400 MHz, CDCl ): δ = 27.4, 37.6, 178.4.
3
(12) Von Gersdorff, J.; Kirste, B.; Niethammer, D.; Harrer, W.;
Kurreck, H. Magn. Reson. Chem. 1988, 26, 416.
HRMS–TOF (CI, MeOH): m/z [M – H]– calcd for C10H15O : 197.0819;
4
found: 197.0816.
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0
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(
1
(
(
(
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©
Georg Thieme Verlag Stuttgart · New York — Synthesis 2015, 47, 2185–2187