Full Papers
doi.org/10.1002/ejoc.202100564
°
hyl acetate (3:1, 10 mL) and heated under 60 C, so the product
3-((4-Fluorophenyl)(phenyl)
methyl)-4-hydroxy-2H-chromen-2-one (3f)
and ionic liquids were extracted and separated. The Schlenk tube
containing ionic liquids was then dried and used directly for the
next cycle.
White solid, 159.8 mg, 92% yield; Melting point: 164–165 C; 1H
NMR (600 MHz, CDCl3) δ 7.73 (dd, J=7.9, 1.3 Hz, 1H), 7.57–7.52 (m,
1H), 7.40 (t, J=7.4 Hz, 2H), 7.34 (dd, J=13.1, 7.6 Hz, 2H), 7.25 (s,
5H), 7.07 (t, J=8.6 Hz, 2H), 6.19 (s, 1H), 5.95 (s, 1H). 13C NMR
(151 MHz, CDCl3) δ 163.1, 161.3, 160.6, 152.7, 140.0, 135.3, 132.3,
130.5, 130.4, 129.7, 128.6, 128.1, 124.0, 123.2, 116.3 (t, J=21.2 Hz),
115.8, 107.6, 46.6. HRMS-ESI: Calcd. For C22H16O3: 346.1005, Found
[M+Na]+: 369.0893.
°
Characterization of the products[14–22]
4-Hydroxy-3-(phenyl(p-tolyl)methyl)-2H-chromen-2-one (3a)
White solid, 164.3 mg, 96% yield; Melting point: 146–147 C; 1H
°
NMR (400 MHz, CDCl3) δ 7.76–7.69 (m, 1H), 7.53 (ddd, J=8.7, 7.4,
1.6 Hz, 1H), 7.41–7.34 (m, 2H), 7.33–7.23 (m, 5H), 7.17 (q, J=8.2 Hz,
4H), 6.33 (dd, J=7.4, 2.8 Hz, 1H), 5.93 (s, 1H), 2.35 (s, 3H). 13C NMR
(101 MHz, CDCl3) δ 163.2, 160.7, 152.8, 140.1, 137.7, 137.0, 132.1,
130.3, 129.4, 128.8, 128.7, 127.7, 123.9, 123.2, 116.5, 116.0, 107.9,
47.0, 21.1. HRMS-ESI: Calcd. For C23H18O3: 342.1256. Found
[M+Na]+: 365.1148.
3-((4-Chlorophenyl)(phenyl)
methyl)-4-hydroxy-2H-chromen-2-one (3g)
White solid, 147.1 mg, 81% yield; Melting point: 151–152 C; 1H
NMR (400 MHz, CDCl3) δ 7.74 (d, J=7.9 Hz, 1H), 7.55 (t, J=7.8 Hz,
1H), 7.36 (dt, J=15.5, 7.4 Hz, 6H), 7.28–7.20 (m, 5H), 6.30 (s, 1H),
5.94 (s, 1H). 13C NMR (101 MHz, CDCl3) δ 163.1, 160.8, 152.7, 139.8,
138.2, 133.5, 132.3, 130.2, 129.7, 129.4, 128.6, 128.2, 124.0, 123.2,
116.5, 115.8, 107.3, 46.7. HRMS-ESI: Calcd. For C22H15ClO3: 362.0710,
Found [M+Na]+: 385.0598.
°
4-Hydroxy-3-(phenyl(o-tolyl)methyl)-2H-chromen-2-one (3b)
White solid, 133.5 mg, 78% yield; Melting point: 161–162 C; 1H
°
NMR (400 MHz, CDCl3) δ 7.72 (d, J=7.9 Hz, 1H), 7.54 (dd, J=11.4,
4.2 Hz, 1H), 7.34 (ddd, J=21.2, 15.9, 7.0 Hz, 6H), 7.20 (dd, J=17.4,
9.5 Hz, 3H), 7.02 (d, J=7.6 Hz, 1H), 6.37 (s, 1H), 6.01 (s, 1H), 2.32 (s,
3H). 13C NMR (101 MHz, CDCl3) δ 163.0, 161.0, 152.7, 139.8, 138.6,
138.1, 132.1, 131.7, 129.5, 128.8, 128.0, 127.8, 127.4, 127.0, 123.9,
123.2, 116.5, 115.8, 106.5, 45.2, 19.7. HRMS-ESI: Calcd. For C23H18O3:
342.1244. Found [M+Na]+: 365.1136.
3-((4-Bromophenyl)(phenyl)
methyl)-4-hydroxy-2H-chromen-2-one (3h)
White solid, 135.2 mg, 66% yield; Melting point: 176–177 C; 1H
NMR (400 MHz, CDCl3) δ 7.73 (d, J=7.9 Hz, 1H), 7.58–7.47 (m, 3H),
7.37 (dt, J=19.2, 7.9 Hz, 4H), 7.25 (d, J=8.7 Hz, 3H), 7.17 (d, J=
7.6 Hz, 2H), 6.19 (s, 1H), 5.93 (s, 1H). 13C NMR (101 MHz, CDCl3) δ
163.1, 160.7, 152.7, 139.7, 138.7, 132.4, 132.3, 130.5, 129.8, 128.6,
128.2, 124.0, 123.2, 121.7, 116.5, 115.8, 107.3, 46.8. HRMS-ESI: Calcd.
For C22H15BrO3: 406.0205, Found [M+Na]+: 429.0088.
°
4-Hydroxy-3-((4-methoxyphenyl)(phenyl)
methyl)-2H-chromen-2-one (3c)
1
°
Orange solid, 175.3 mg, 98% yield; Melting point: 87–88 C; H NMR
(600 MHz, CDCl3) δ 7.73 (d, J=7.9 Hz, 1H), 7.53 (t, J=7.8 Hz, 1H),
7.38 (t, J=7.4 Hz, 2H), 7.34–7.30 (m, 2H), 7.28 (d, J=8.1 Hz, 3H), 7.18
(d, J=8.5 Hz, 2H), 6.91 (d, J=8.7 Hz, 2H), 6.31 (s, 1H), 5.91 (s, 1H),
3.81 (s, 3H). 13C NMR (151 MHz, CDCl3) δ 163.3, 160.6, 159.2, 152.7,
140.2, 132.1, 131.7, 129.9, 129.4, 128.7, 127.7, 123.9, 123.2, 116.5,
116.0, 114.9, 107.9, 55.3, 46.6. HRMS-ESI: Calcd. For C23H18O4:
358.1205. Found [M+Na]+: 381.1099.
4-Hydroxy-3-(phenyl(4-(trifluoromethyl)phenyl)
methyl)-2H-chromen-2-one (3i)
White solid, 159.6 mg, 81% yield; Melting point: 158–159 C; 1H
NMR (400 MHz, CDCl3) δ 7.75 (d, J=7.9 Hz, 1H), 7.63 (d, J=7.9 Hz,
2H), 7.56 (t, J=7.8 Hz, 1H), 7.37 (ddd, J=27.9, 16.9, 8.8 Hz, 6H),
7.27–7.21 (m, 3H), 6.30 (s, 1H), 6.03 (s, 1H). 13C NMR (101 MHz,
CDCl3) δ 163.1, 161.0, 152.7, 143.8, 139.5, 132.5, 129.9, 129.3, 128.7,
128.4, 126.1 (q, J=7.41 Hz), 125.4, 124.1, 123.2, 122.7, 116.6, 115.7,
107.0, 47.2. HRMS-ESI: Calcd. For C23H15F3O3: 396.0973, Found [M+
Na]+: 419.0861.
°
3-(Bis(4-methoxyphenyl)methyl)-4-hydroxy-2H-chromen-2-one
(3d)
Reddish orange solid, 191.5 mg, 99% yield; Melting point: 148–
1
°
149 C; H NMR (400 MHz, CDCl3) δ 7.73 (d, J=7.8 Hz, 1H), 7.53 (t,
3-(Bis(4-chlorophenyl)methyl)-4-hydroxy-2H-chromen-2-one (3j)
J=7.7 Hz, 1H), 7.33–7.15 (m, 6H), 6.90 (d, J=8.5 Hz, 4H), 6.39 (s, 1H),
5.84 (s, 1H), 3.81 (s, 6H). 13C NMR (101 MHz, CDCl3) δ 163.2, 160.5,
159.1, 152.7, 132.01, 132.0, 129.8, 123.9, 123.1, 116.4, 116.0, 114.8,
113.4, 108.0, 55.3, 45.8. HRMS-ESI: Calcd. For C24H20O5: 388.1311,
Found [M+Na]+: 411.1200.
White solid, 123.5 mg, 62% yield; Melting point: 177–178 C; 1H
°
NMR (600 MHz, CDCl3) δ 7.73 (dd, J=7.9, 1.1 Hz, 1H), 7.58–7.52 (m,
1H), 7.40 (t, J=7.4 Hz, 2H), 7.34 (dt, J=16.5, 5.9 Hz, 4H), 7.26–7.19
(m, 4H), 6.21 (s, 1H), 5.94 (s, 1H). 13C NMR (151 MHz, CDCl3) δ 163.1,
160.7, 152.7, 139.80, 138.2, 133.6, 132.3, 130.2, 129.8, 129.5, 128.7,
128.2, 124.0, 123.2, 116.5, 115.8, 107.4, 46.8. HRMS-ESI: Calcd. For
C22H14Cl2O3: 396.0320, Found [M+Na]+: 419.0208.
3-Benzhydryl-4-hydroxy-2H-chromen-2-one (3e)
White solid, 157.8 mg, 96% yield; Melting point: 154–156 C; 1H
NMR (400 MHz, CDCl3) δ 7.73 (dd, J=8.0, 1.5 Hz, 1H), 7.54 (ddd, J=
8.8, 7.4, 1.6 Hz, 1H), 7.42–7.36 (m, 4H), 7.36–7.30 (m, 3H), 7.30–7.26
(m, 5H), 6.22 (s, 1H), 5.99 (s, 1H). 13C NMR (101 MHz, CDCl3) δ 163.2,
152.7, 139.9, 132.2, 129.5, 128.8, 127.9, 123.9, 123.2, 116.5, 115.9,
107.7, 107.1, 47.4. HRMS-ESI: Calcd. For C22H15FO3: 328.1099, Found
[M+Na]+: 351.0994.
°
3-([1,1’-Biphenyl]-4-yl(phenyl)
methyl)-4-hydroxy-2H-chromen-2-one (3k)
White solid, 163.2 mg, 81% yield; Melting point: 181–182 C; 1H
°
NMR (400 MHz, CDCl3) δ 7.75 (d, J=7.9 Hz, 1H), 7.66–7.51 (m, 5H),
7.47–7.25 (m, 12H), 6.35 (s, 1H), 6.02 (s, 1H). 13C NMR (101 MHz,
CDCl3) δ 163.2, 160.7, 152.7, 140.7, 140.3, 140.0, 138.8, 132.2, 129.5,
129.2, 128.83, 128.77, 128.1, 127.9, 127.5, 127.0, 124.0, 123.2, 116.5,
Eur. J. Org. Chem. 2021, 3819–3826
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