supporting information synthesis of long …1 supporting information synthesis of long-chain polyols...
TRANSCRIPT
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SUPPORTING INFORMATION
Synthesis of long-chain polyols from the Claisen condensation of -valerolactone
Camila S. Santos[a], Caio Soares[b], Adriano Siqueira[c] and Antonio C. B. Burtoloso*[a]
Contents Page
Derivatization of compound 3 2-3
1H and 13C NMR spectra of all products 5-36
Electronic Supplementary Material (ESI) for Green Chemistry.This journal is © The Royal Society of Chemistry 2019
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Derivatization of compound 3 for GC-MS analysis
Compound 3 (5 mg, 0,024 mmol), 0.5 mL of dry 2 Methyltetrahydrofuranand and 200 µL
of N,O-Bis(trimethylsilyl)trifluoroacetamide (BSTFA) were added to a 25 mL round
bottom flask. Next, the reaction was heated at 60°C during 2h. The system was cooled
to 25 °C and a 100 µL aliquot of the reaction medium was diluted in 5 mL of
dichloromethane. An aliquot of this solution was filtered off (Chromafil, Macherey-
Nagel, pore size 0.45μm) and injected into GC-MS. GC-MS analyses were carried out on
Shimadzu-CGMS QP 2010 ULTRA gas chromatography on RESTEK Rtx-5MS
5%diphenyl/95% dimethyl polysiloxane capillary Column 30 m × 0.25 mm, 0.25 μm, split
injector, entrained gas flow (He) 1.33 mL/min, injector 300 °C, interface 330 °C. Column
temperature was started from 45 °C maintained for 1 minute and increased to 170 °C
at the rate of 10 °C/min, remaining constant for 3 mim. Then, was heated to 330 °C at
the rate of 10 °C/min.
Figure 2. GC-MS chromatogram of silylated compound 3.
A)
B)
m/z= 247 (M+ - 247)
m/z= 247 (M+ - 247)
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Figure 3. Fragmentation of peaks with retention time A) 20.213, B) 20.280, C) 20.354, D)20.403.
C)
D)
m/z= 247 (M+ - 247)
m/z= 247 (M+ - 247)
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture
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Diastereisomeric mixture