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14
General Procedure
for the Synthesis of 1a
Diethyl acetylenedicarboxylate
(2 mmol), prop-2-yn-1-ol (2 mmol), DABCO (0.2 mmol) in CH2Cl2 were
stirred for 10 min at r.t. And then the solution was evaporated
to dryness under reduced pressure. Subsequently, CuI (10% mmol)
and DMF were added at 80 ˚C. After completion
of the reaction (monitored by TLC), the solution was evaporated
to dryness under reduced pressure, and then H2O (10 mL)
was added. The aqueous solution was extracted with Et2O
(3 × 10 mL), and the combined extract
was dried with anhyd MgSO4. The solvent was removed,
and the crude product was separated by column chromatography to
give a pure sample of 1a.
15
General Procedure
for the Synthesis of 1c
Diethyl acetylenedicarboxylate
(2 mmol), prop-2-yn-1-ol (2 mmol), DABCO (0.2 mmol) in CH2Cl2 were
stirred for 10 min at r.t. And then the solution was evaporated
to dryness under reduced pressure. Subsequently, AgOAc/Ph3P
and toluene were added at 50 ˚C. After completion
of the reaction (monitored by TLC), the solution was evaporated
to
dryness under reduced pressure, and then H2O (10 mL) was
added. The aqueous solution was extracted with Et2O (3 × 10
mL), and the combined extract was dried with anhyd MgSO4.
The solvent was removed, and the crude product was separated by
column chromatography to give a pure sample of 1c.
16
General Procedure
for the Synthesis of 3a
To the mixture of Pd(OAc)2 (5% mol),
Ph3P (10% mol), Cs2CO3 (1.0
mmol), 1a (0.5 mmol), 2a (0.7
mmol), and DMP (4 mL) were added successively. The mixture was stirred
at 120 ˚C for 20 hours. The solution was extracted with
EtOAc (3 × 15 mL), and the combined extract
was dried with anhyd MgSO4. Solvent was removed, and
the residue was separated by column chromatography to give the pure
sample 3a.
Diethyl
5-Formyl-4-phenylfuran-2,3-dicarboxylate (3a)
¹H
NMR (400 MHz, CDCl3): δ = 9.70 (s,
1 H), 7.47 (s, 5 H), 4.43 (q, J = 8.0
Hz, 2 H), 4.28 (q, J = 8.0
Hz, 2 H), 1.40 (t, J = 8.0
Hz, 3 H), 1.22 (q, J = 8.0
Hz, 3 H). ¹³C NMR (100 MHz, CDCl3): δ = 178.0,
162.0, 157.1, 147.5, 144.3, 136.1, 129.7, 129.5, 128.7, 127.5, 126.3,
62.3, 62.1, 14.0, 13.7.
MS (EI): m/z (%) = 316,
288, 225, 213, 170, 115, 77.
