I
I. Sato et al.
Feature
Synthesis
HRMS (DART): m/z [M + NH4]+ calcd for C22H26N: 304.20652; found:
304.20517.
1H NMR (CDCl3, 500 MHz): = 7.79–7.77 (3 H, m), 7.67 (2 H, d, J = 8.50
Hz), 7.58 (2 H, d, J = 7.94 Hz), 7.40 (4 H, tt, J = 24.37, 10.11 Hz), 7.20–
7.02 (8 H, m), 4.34–4.32 (1 H, m), 3.62–3.60 (1 H, m), 3.44–3.42 (1 H,
m), 3.16–3.14 (2 H, m).
4,4′-(3-Phenylpropane-1,2-diyl)bis(tert-butylbenzene) (3ab)
13C NMR (CDCl3, 125 MHz): = 141.28, 140.33, 136.19, 133.79,
132.04, 129.24, 128.75, 128.65, 128.63, 128.10, 126.96, 126.65,
126.59, 125.96, 125.70, 125.43, 125.40, 125.24, 125.13, 125.10,
125.07, 123.57, 123.52, 122.62, 42.61, 41.08, 38.78.
HRMS (DART): m/z [M + H]+ calcd for C29H25: 373.19563; found:
373.19747.
Condition A; scale: 0.3 mmol; catalyst loading: 10 mol%; tempera-
ture: 0 °C; time: 18 h; white solid; yield: 115.7 mg (~100%); mp 82–
84 °C; Rf = 0.5 (hexane/CH2Cl2 4:1).
IR (neat): 698, 729, 746, 774, 789, 1395, 1453, 1495, 1509, 1596 cm–1
.
1H NMR (CDCl3, 500 MHz): = 7.15–7.12 (4 H, m), 7.08–7.06 (2 H, m),
7.03–7.00 (1 H, m), 6.94–6.88 (6 H, m), 3.08–3.03 (1 H, m), 2.87–2.75
(4 H, m), 1.20 (9 H, s), 1.20 (9 H, s).
13C NMR (CDCl3, 125 MHz): = 148.72, 148.46, 141.62, 140.73,
137.61, 129.14, 128.73, 127.92, 127.35, 125.62, 124.94, 124.92, 48.73,
42.10, 41.74, 34.31, 34.30, 31.39, 31.38.
[2-(4-Methoxyphenyl)propane-1,3-diyl]dibenzene (3af)
Condition A; scale: 0.6 mmol; catalyst loading: 5 mol%; temperature:
0 °C; time: 24 h; colorless oil; yield: 174.9 mg (96%); : = 1:12; Rf =
0.1 (hexane/CH2Cl2 4:1).
HRMS (DART): m/z [M + H]+ calcd for C29H37: 385.28953; found:
385.29087.
IR (neat): 598, 696, 746, 772, 821, 908, 1031, 1029, 1109, 1176, 1243,
1300, 1395, 1452, 1495, 1510 cm–1
.
1H NMR (CDCl3, 500 MHz): = 7.20–7.16 (4 H, m), 7.13–7.11 (2 H, m),
7.00–6.99 (4 H, m), 6.95–6.94 (2 H, m), 6.74–6.73 (2 H, m), 3.74 (3 H,
s), 3.10–3.06 (1 H, m), 2.95 (2 H, dd, J = 6.61, 3.31 Hz), 2.86 (2 H, dd, J =
13.32, 8.22 Hz).
13C NMR (CDCl3, 125 MHz): = 157.77, 140.56, 136.24, 129.11,
128.70, 128.01, 125.73, 113.42, 55.10, 48.99, 42.62.
3,3′-(3-Phenylpropane-1,2-diyl)bis(methoxybenzene) (3ac)
Condition A; scale: 0.3 mmol; catalyst loading: 10 mol%; tempera-
ture: 0 °C; time: 18 h; colorless oil; yield: 84.8 mg (85%); Rf = 0.1 (hex-
ane/CH2Cl2 3:2).
IR (neat): 474, 504, 571, 695, 741, 754, 776, 872, 1042, 1152, 1256,
1286, 1315, 1435, 1452, 1486, 1583, 1599 cm–1
.
HRMS (DART): m/z [M + H]+ calcd for C22H23O: 303.17489; found:
303.17435.
1H NMR (CDCl3, 500 MHz): = 7.24–7.21 (2 H, m), 7.16–7.15 (3 H, m),
7.05 (2 H, d, J = 7.94 Hz), 6.72 (3 H, d, J = 7.94 Hz), 6.67 (1 H, d, J = 7.37
Hz), 6.63 (1 H, s), 6.58 (1 H, s), 3.74 (3 H, s), 3.73 (3 H, s), 3.19–3.13 (1
H, m), 2.99–2.93 (4 H, m).
13C NMR (CDCl3, 125 MHz): = 159.30, 159.27, 145.93, 141.99,
140.36, 129.08, 129.00, 128.96, 128.02, 125.79, 121.53, 120.26,
114.73, 113.72, 111.31, 111.22, 55.04, 55.00, 49.68, 42.32, 42.28.
1-Methoxy-2-[2-(4-methoxyphenyl)-3-phenylpropyl]benzene
(3bf)
Condition B; scale: 0.6 mmol; catalyst loading: 5 mol%; temperature:
0 °C; time: 18 h; colorless oil; yield: 173.6 mg (87%); : = 1:12; Rf =
0.1 (hexane/CH2Cl2 4:1).
HRMS (DART): m/z [M + H]+ calcd for C23H25O2: 333.18545; found:
333.18379.
IR (neat): 546, 601, 698, 748, 824, 1031, 1105, 1176, 1239, 1438,
1492, 1510, 1585 cm–1
.
1H NMR (CDCl3, 500 MHz): = 7.15–7.07 (4 H, m), 6.99–6.93 (4 H, m),
6.89 (1 H, d, J = 7.37 Hz), 6.77–6.68 (4 H, m), 3.70 (3 H, s), 3.70 (3 H, s),
3.20–3.14 (1 H, m), 3.00–2.96 (2 H, m), 2.87–2.83 (2 H, m).
13C NMR (CDCl3, 125 MHz): = 157.59, 157.51, 140.89, 136.87,
130.70, 129.09, 129.02, 128.66, 127.83, 126.96, 125.51, 120.02,
113.23, 110.12, 55.11, 55.04, 47.04, 42.52, 37.13.
4,4′-(3-Phenylpropane-1,2-diyl)bis(methoxybenzene) (3ad)
Condition A; scale: 0.4 mmol; catalyst loading: 10 mol%; KOt-Bu and
LiTMP were used instead of KCH2TMS; temperature: 60 °C; time: 24
h; colorless oil; yield: 137.2 mg (~100%); Rf = 0.3 (hexane/CH2Cl2 2:1).
IR (neat): 3060, 3028, 3001, 2927, 2836, 1610, 1584, 1511, 1459,
1298, 1178, 1107, 1036 cm–1
.
HRMS (DART): m/z [M + H]+ calcd for C23H25O2: 333.18545; found:
333.18666.
1H NMR (CDCl3, 500 MHz): = 7.18–7.16 (2 H, m), 7.11–7.10 (1 H, m),
6.98 (2 H, d, J = 6.80 Hz), 6.93 (2 H, d, J = 8.50 Hz), 6.89 (2 H, d, J = 8.50
Hz), 6.74–6.72 (4 H, m), 3.73 (3 H, s), 3.73 (3 H, s), 3.06–3.01 (1 H, m),
2.96–2.78 (4 H, m).
13C NMR (CDCl3, 125 MHz): = 157.75, 157.63, 140.64, 136.35,
132.60, 129.99, 129.10, 128.72, 127.98, 125.68, 113.40, 113.39, 55.09,
55.06, 49.15, 42.52, 41.72.
1-Methoxy-3-[2-(4-methoxyphenyl)-3-phenylpropyl]benzene
(3cf)
Condition B; scale: 0.6 mmol; catalyst loading: 5 mol%; temperature:
0 °C; time: 18 h; colorless oil; yield: 194.0 mg (97%); : = 1:10; Rf =
0.1 (hexane/CH2Cl2 2:1).
HRMS (DART): m/z [M + H]+ calcd for C23H25O2: 333.18491; found:
333.18418.
IR (neat): 599, 696, 774, 826, 908, 1029, 1078, 1029, 1243, 1395,
1452, 1510, 1582, 1596 cm–1
.
1H NMR (CDCl3, 500 MHz): = 7.20–7.16 (2 H, m), 7.11–7.09 (2 H, m),
6.99–6.95 (4 H, m), 6.73 (2 H, d, J = 7.37 Hz), 6.66 (1 H, d, J = 7.94 Hz),
6.60 (1 H, d, J = 7.37 Hz), 6.52 (1 H, s), 3.72 (3 H, s), 3.68 (3 H, s), 3.09–
3.07 (1 H, m), 2.94–2.92 (2 H, m), 2.87–2.82 (2 H, m).
13C NMR (CDCl3, 125 MHz): = 159.24, 157.77, 142.15, 140.49,
136.22, 129.10, 128.92, 128.68, 127.99, 125.72, 121.54, 114.75,
113.42, 111.13, 55.07, 54.97, 48.79, 42.62, 42.60.
1,1′-(3-Phenylpropane-1,2-diyl)dinaphthalene (3ae)
Condition A; scale: 0.4 mmol; catalyst loading: 10 mol%; tempera-
ture: 0 °C; time: 48 h; colorless oil; yield: 113.2 mg (76%); Rf = 0.2
(hexane/CH2Cl2 9:1).
IR (neat): 698, 729, 772, 908, 1395, 1452, 1495, 1029, 1596 cm–1
.
Georg Thieme Verlag Stuttgart · New York — Synthesis 2018, 50, A–K