Supporting Information
Phenylsulfonylacetic Acid: Condensations onto Aryl Aldehydes
David C. Forbes,* Mike S. South, Rajesh Rengasamy, Adirika J. Obiako, and David R. Battiste
Department of Chemistry, University of South Alabama, Mobile, Alabama 36688
*corresponding author: dforbes@southalabama.edu
S1 – Table of Contents
S2 – General Experimental Considerations
S3 – Representative Procedure
S4 – 1H NMR of 3-[(1E)-2-(phenylsulfonyl)ethenyl]pyridine
S5 – 13C NMR of 3-[(1E)-2-(phenylsulfonyl)ethenyl]pyridine
S6 – 1H NMR of 2-[(1E)-2-(phenylsulfonyl)ethenyl]furan
S7 – 13C NMR of 2-[(1E)-2-(phenylsulfonyl)ethenyl]furan
S8 – 1H NMR of 1-chloro-4-[(1E)-2-(phenylsulfonyl)ethenyl]benzene
S9 – 13C NMR of 1-chloro-4-[(1E)-2-(phenylsulfonyl)ethenyl]benzene
S10– 1H NMR of 1,3-dichloro-2-[(1E)-2-(phenylsulfonyl)ethenyl]benzene
S11 – 13C NMR of 1,3-dichloro-2-[(1E)-2-(phenylsulfonyl)ethenyl]benzene
S12 – 1H NMR of E-[2-(phenylsulfonyl)ethenyl]benzene
S13 – 13C NMR of E-[2-(phenylsulfonyl)ethenyl]benzene
S14 – 1H NMR of 4-[(1E)-2-(phenylsulfonyl)ethenyl]-1,3-benzodioxole
S15 – 13C NMR of 4-[(1E)-2-(phenylsulfonyl)ethenyl]-1,3-benzodioxole
S16 – 1H NMR of 1-methoxy-4-[(1E)-2-(phenylsulfonyl)ethenyl]benzene
S17 – 13C NMR of 1-methoxy-4-[(1E)-2-(phenylsulfonyl)ethenyl]benzene
S1
General Experimental Considerations
1H
NMR (300 MHz) and
13C
NMR (75 MHz) spectra were
obtained as solutions in CDCl3. Chemical shifts were reported in parts per million (ppm, ) and
referenced to  7.27 (1H NMR) and  77.00 (13C NMR) when using CDCl3. Infrared spectra were
recorded as thin films and were reported in wavenumbers (cm-1). TLC analyses were performed on
Whatman flexible aluminium backed TLC plates with a fluorescent indicator. Detection was conducted
by UV absorption (254 nm) and charring with 10% KMnO4 in water. High-purity grade silica gel
(Merck Grade 7734), pore size 60 Å, 70-230 mesh was used for all chromatographic separations. All
chemicals used for synthetic procedures were reagent grade or better. Solutions were concentrated in
vacuo with a rotary evaporator and the residue was purified using a silica gel column unless specified
otherwise.
S2
Representative Procedure A 50 mL one-neck round bottomed flask equipped with a magnetic stir bar
was fitted with a water-jacketed condenser. To a solution of phenylsulfonylacetic acid (1.0 g, 4.99
mmol, 2.0 equiv) in THF (0.125M, 20mL) was added in one portion aldehyde (2.5 mmol, 1.0 equiv). A
40 wt% solution of benzyltrimethylammonium hydroxide in methanol was next added by syringe (2.1
mL, 4.99 mmol, 2.0 equiv). The reaction mixture was allowed to warm to reflux. After a period of 18h,
the solution was cooled to 60°C and 15 mL of deionized water was added an allowed to stir at this
temperature for a period of 1h. The resulting mixture was allowed to cool to room temperature at which
time the mixture was washed with approximately 20 mL of ethyl acetate. After partitioning the organic
from the aqueous phase, the organic fraction was washed with brine, dried over anhydrous magnesium
sulfate, and concentrated in vacuo. Purification by column chromatography over silica gel (eluting with
9:1 petroleum ether/ethyl acetate) afforded the title compounds.
S3
S4
S5
S6
S7
S8
S9
S10
S11
S12
S13
S
O
O
O
O
S14
S
O
O
O
O
S15
S
O
H3CO
O
S16
S
O
H3CO
O
S17