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(26) To a solution of benzyl alcohol (4.6 mmol) in DMSO (2 mL), T3P®
(5.5 mmol, 50% solution in EtOAc) was added at 0 °C followed
by Et3N (9.2 mmol) under nitrogen atmosphere. The mixture
was stirred at r.t. for 1.5 h. After completion of the reaction
(monitored by TLC), KOH (69.0–92.0 mmol) in H2O–EtOH
mixture (3 mL, 1:1, v/v) was added dropwise to the reaction
mixture at 0 °C and stirred for 5 min followed by TosMIC (5.0
mmol) addition. The reaction was monitored by TLC and evapo-
rated the EtOH from reaction mixture under reduced pressure,
followed by dilution with EtOAc (2 × 25 mL). The organic layer
was washed with H2O (2 × 20 mL) and brine solution (2 × 20
mL). Then, the organic layer was dried over anhydrous Na2SO4
and concentrated in vacuum to afford crude product. The crude
was purified by column chromatography over silica gel (60–120
mesh) using hexane–EtOAc mixture as eluent (8:2) and
obtained 3a (83% yield) as pale yellow solid; mp 37–39 °C. FTIR:
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3013, 3006, 2988, 2251, 1661, 1052, 1024, 1005, 658 cm–1 1H
.
NMR (400 MHz, CDCl3): δ = 7.89 (s, 1 H, ArH), 7.65-7.62 (m, 2 H,
ArH), 7.43–7.38 (m, 2 H, ArH), 7.34–7.30 (m, 2 H, ArH). 13C NMR
(100 MHz, CDCl3): δ = 151.5, 150.3, 128.9, 128.6, 127.7, 124.3,
121.4. HRMS: m/z calcd: 145.158; found: 146.703 [M + H]+.
Anal. Calcd for C9H7NO: C, 74.47; H, 4.86; N, 9.65; O, 11.02.
Found: C, 74.48; H, 4.89; N, 9.66.
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(27) CCDC 1429231 contains the supplementary crystallographic
data for this paper. The data can be obtained free of charge from
The
Cambridge
Crystallographic
Data
Centre
via
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(28) The mixture of benzyl bromide (2.9 mmol) and NaHCO3 (4.3
mmol) was stirred for 5 min followed by the addition of DMSO
(1 mL) at r.t., and the reaction was monitored by TLC, followed
by dropwise addition of KOH (4.3–5.8 mmol) in H2O–EtOH
mixture (3 mL, 1:1, v/v) at 0 °C. The reaction mixture was
stirred for 5 min followed by the addition of TosMIC (5.0 mmol),
then continued the stirring for 2–3 h. After completion of the
reaction, EtOH was removed under reduced pressure; extracted
and purified the crude product 3a as mentioned the above pro-
cedure. The characterisation data were identical with the prod-
ucts isolated in the earlier protocol.
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© Georg Thieme Verlag Stuttgart · New York — Synlett 2016, 27, A–D