F
J. Gu et al.
Paper
Synthesis
1H NMR (500 MHz, CDCl3): δ = 6.90–6.78 (m, 3 H), 6.32 (d, J = 16.0 Hz,
1 H), 6.03 (dd, J = 7.0, 16.0 Hz, 1 H), 4.00–3.98 (m, 2 H), 3.89 (s, 3 H),
3.85 (s, 3 H), 3.47–3.42 (m, 2 H), 2.37–2.32 (m, 1 H), 1.70–1.67 (m, 2
H), 1.59–1.51 (m, 2 H).
13C NMR (125 MHz, CDCl3): δ = 153.6, 148.9, 148.5, 130.8, 130.2,
128.9, 128.2, 126.8, 125.3, 124.7, 119.2, 111.0, 108.5, 84.8, 82.2, 55.8,
55.7, 49.9, 36.5, 27.7.
HRMS (ESI): m/z [M + Na]+ calcd for C24H29O5Na: 419.1829; found:
419.1831.
13C NMR (125 MHz, CDCl3): δ = 148.9, 148.3, 132.6, 130.5, 127.7,
118.9, 111.0, 108.3, 67.6, 55.8, 55.7, 38.2, 32.6.
HRMS (ESI): m/z [M + H]+ calcd for C15H21O3: 249.1490; found:
3-(Prop-1-en-2-yl)-1-tosylpyrrolidine (26)
249.1486.
According to the general procedure, column chromatography (silica
gel, 7% EtOAc/PE) gave the product (25.9 mg, 0.097 mmol, 65%) as a
white solid; mp 45–46 °C.
(E)-6-(2-Cyclohexylvinyl)-2,3-dihydro-1,4-benzodioxine (22)
According to the general procedure, column chromatography (silica
gel, 2% EtOAc/PE) gave the product (23.8 mg, 0.097 mmol, 65%) as a
colorless oil.
1H NMR (500 MHz, CDCl3): δ = 6.87–6.77 (m, 3 H), 6.23 (d, J = 16.0 Hz,
1 H), 6.02 (dd, J = 7.0, 16.0 Hz, 1 H), 4.24 (s, 4 H), 2.11–2.05 (m, 1 H),
1.79–1.74 (m, 4 H), 1.32–1.12 (m, 6 H).
1H NMR (500 MHz, CDCl3): δ = 7.72 (d, J = 8.0 Hz, 2 H), 7.32 (d, J = 8.0
Hz, 2 H), 4.72 (s, 1 H), 4.62 (s, 1 H), 3.50–3.47 (m, 1 H), 3.43–3.38 (m, 1
H), 3.25–3.20 (m, 1 H), 3.01 (t, J = 9.5 Hz, 1 H), 2.63–2.55 (m, 1 H), 2.43
(s, 3 H), 1.95–1.90 (m, 1 H), 1.65 (s, 3 H), 1.62–1.56 (m, 1 H).
13C NMR (125 MHz, CDCl3): δ = 143.6, 143.3, 133.9, 129.6, 127.6,
110.6, 51.5, 47.6, 45.0, 29.9, 21.5, 21.0.
13C NMR (125 MHz, CDCl3): δ = 143.4, 142.5, 135.3, 131.9, 126.3,
HRMS (ESI): m/z [M + H]+ calcd for C14H20NO2S: 266.1215; found:
119.2, 117.1, 114.3, 64.3, 64.3, 41.0, 32.9, 26.1, 26.0.
266.1216.
HRMS (ESI): m/z [M + H]+ calcd for C16H21O2: 245.1542; found:
245.1542.
(E)-3-Methyl-5-phenylpent-4-enyl 4-Methoxybenzoate (27)
According to the general procedure, purification by column chroma-
tography (silica gel, 3% EtOAc/PE) gave the product (39.1 mg, 0.126
mmol, 84%) as a colorless oil.
1H NMR (500 MHz, CDCl3): δ = 8.01 (d, J = 9.0 Hz, 2 H), 7.36 (d, J = 7.5
Hz, 2 H), 7.31 (t, J = 7.5 Hz, 2 H), 7.22 (t, J = 7.5 Hz, 1 H), 6.90 (d, J = 9.0
Hz, 2 H), 6.43 (d, J = 16.0 Hz, 1 H), 6.14 (dd, J = 8.0, 16.0 Hz, 1 H), 4.38–
4.32 (m, 2 H), 3.85 (s, 3 H), 2.59–2.53 (m, 1 H), 1.90–1.84 (m, 2 H),
1.19 (d, J = 6.8 Hz, 3 H).
(E)-4-(2-Cyclohexylvinyl)-1,2-dimethoxybenzene (23)
According to the general procedure, column chromatography (silica
gel, 10% EtOAc/PE) gave the product (25.8 mg, 0.105 mmol, 70%) as a
white solid; mp 85–86 °C.
1H NMR (500 MHz, CDCl3): δ = 6.93–6.88 (m, 2 H), 6.82 (d, J = 8.0 Hz, 1
H), 6.32 (d, J = 16.0 Hz, 1 H), 6.07 (dd, J = 7.0, 16.0 Hz, 1 H), 3.92 (s, 3
H), 3.89 (s, 3 H), 2.16–2.09 (m, 1 H), 1.84–1.77 (m, 4 H), 1.37–1.16 (m,
6 H).
13C NMR (125 MHz, CDCl3): δ = 166.2, 163.1, 137.4, 135.3, 131.4,
128.8, 128.4, 126.9, 126.0, 113.4, 63.0, 55.3, 35.7, 34.4, 20.6.
HRMS (ESI): m/z [M + NH4]+ calcd for C20H26NO3: 328.1912; found:
13C NMR (125 MHz, CDCl3): δ = 148.9, 148.1, 135.0, 131.1, 126.8,
118.8, 111.1, 108.4, 55.9, 55.7, 41.1, 33.1, 26.2, 26.1.
328.1909.
HRMS (ESI): m/z [M + H]+ calcd for C16H23O2: 247.1698; found:
247.1698.
(E)-2-(3-Methyl-5-phenylpent-1-enyl)naphthalene (28)
According to the general procedure, purification by column chroma-
tography (silica gel, 2% EtOAc/PE) gave the product (22.3 mg, 0.078
mmol, 52%; E/Z 93:7) as a colorless oil.
1H NMR (500 MHz, CDCl3): δ = 7.84–7.81 (m, 3 H), 7.74–7.63 (m, 2 H),
7.49–7.45 (m, 2 H), 7.35–7.32 (m, 2 H), 7.26–7.23 (m, 3 H), 6.60 (d, J =
16.0 Hz, 1 H), 6.29 (dd, J = 8.0, 16.0 Hz, 1 H), 2.76–2.68 (m, 2 H), 2.47–
2.41 (m, 1 H), 1.82–1.78 (m, 2 H), 1.22 (d, J = 6.8 Hz, 3 H).
13C NMR (125 MHz, CDCl3): δ = 142.7, 136.9, 135.3, 132.7, 128.8,
128.5, 128.3, 128.1, 127.8, 127.7, 127.7, 126.2, 125.7, 125.5, 125.5,
123.6, 38.8, 37.1, 33.8, 20.8.
(E)-1-Chloro-4-(2-cyclopentylvinyl)benzene (24)
According to the general procedure, column chromatography (silica
gel, 2% EtOAc/PE) gave the product (13.9 mg, 0.068 mmol, 45%) as a
colorless oil.
1H NMR (500 MHz, CDCl3): δ = 7.26–7.25 (m, 4 H), 7.33 (d, J = 16.0 Hz,
1 H), 6.20 (dd, J = 8.0, 16.0 Hz, 1 H), 2.63–2.56 (m, 1 H), 1.87–1.83 (m,
2 H), 1.72–1.67 (m, 2 H), 1.65–1.58 (m, 2 H), 1.42–1.34 (m, 2 H).
13C NMR (125 MHz, CDCl3): δ = 136.4, 132.2, 129.9, 128.5, 127.1,
126.7, 43.8, 34.1, 33.1, 31.5, 25.2.
HRMS (ESI): m/z [M + H]+ calcd for C13H16Cl: 207.0940; found:
207.0940.
HRMS (ESI): m/z [M + H]+ calcd for C22H23: 287.1800; found:
287.1796.
tert-Butyl 2-[(E)-3,4-Dimethoxystyryl)-2,3-dihydro-1H-inden-1-
yl] Carbonate (25)
7-[(3,4-Dimethylpent-4-enyl)oxy]-4-methyl-2H-chromen-2-one
(29)
According to the general procedure, column chromatography (silica
gel, 10% EtOAc/PE) gave the product (43.4 mg, 0.109 mmol, 73%) as a
white solid; mp 110–111 °C.
1H NMR (500 MHz, CDCl3): δ = 7.44 (d, J = 7.0 Hz, 1 H), 7.34–7.25 (m, 3
H), 6.93–6.90 (m, 2 H), 6.83 (d, J = 8.5 Hz, 1 H), 6.54 (d, J = 16.0 Hz, 1
H), 6.19 (dd, J = 8.0, 16.0 Hz, 1 H), 5.98 (d, J = 4.8 Hz, 1 H), 3.91 (s, 3 H),
3.89 (s, 3 H), 3.37–3.29 (m, 2 H), 2.89–2.86 (m, 1 H), 1.54 (s, 9 H).
According to the general procedure, purification by column chroma-
tography (silica gel, 5% EtOAc/PE) gave the product (24.9 mg, 0.092
mmol, 61%) as a white solid; mp 55–56 °C.
1H NMR (500 MHz, CDCl3): δ = 7.47 (d, J = 9.0 Hz, 1 H), 6.78–6.77 (m, 2
H), 6.10 (s, 1 H), 4.72–4.72 (m, 2 H), 4.01–3.94 (m, 2 H), 2.44–2.41 (m,
1 H), 2.38 (s, 3 H), 1.86–1.78 (m, 2 H), 1.68 (s, 3 H), 1.09 (s, 3 H).
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2017, 49, A–G