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PAPER
HRMS (FAB): m/z (MH+) calcd for C11H14NO3: 208.0974; found:
208.0975.
4¢-[(6-Bromohexyl)oxy]biphenyl-4-yl 3-(4-Methoxyphe-
nyl)acrylate (Entry 11)
This compound was prepared from 3-(4-methoxyphenyl)acrylic
acid and 4¢-[(6-bromohexyl)oxy]biphenyl-4-ol using a THF–
CH2Cl2 mixture as the solvent.
6-{4-[(4-Nitrophenyl)diazenyl]phenoxy}hexyl Acrylate (Entry
7)
This compound was prepared from acrylic acid and 6-{4-[(4-nitro-
phenyl)diazenyl]phenoxy}hexan-1-ol using CH2Cl2 as the solvent.
Yield: 76% (<90 based on recovered alcohol component); colorless
solid; mp 146–148 °C (EtOH).
Yield: 76% (<90 based on recovered alcohol component); colorless
solid; mp 101–103 °C.
1H NMR (CDCl3): d = 1.38–1.47 (m, 4 H), 1.66 (quint, 2 H, J = 6.9
Hz), 1.78 (quint, 2 H, J = 5.7 Hz), 4.00 (t, 2 H, J = 5.6 Hz), 4.11 (t,
2 H, J = 6.5 Hz), 5.76 (dd, 1 H), 6.05 (dd, 1 H), 6.34 (dd, 1 H), 6.94
(d, 2 H, J = 9.0 Hz), 7.85–7.93 (m, 4 H), 8.26 (d, 2 H, J = 9.1 Hz).
13C NMR (CDCl3): d = 25.6, 28.4, 28.9, 64.3, 68.2, 114.8, 123.0,
124.6, 125.5, 128.4, 130.4, 146.7, 148.1, 155.9, 162.7, 166.2.
MS (FAB): m/z = 398.31 (M + H+).
1H NMR (CDCl3): d = 1.43–1.46 (m, 4 H), 1.73–1.76 (m, 2 H)
1.81–1.85 (m, 2 H), 3.35 (t, 2 H), 3.78 (s, 3 H), 3.92 (t, 2 H), 6.44
(dd, 1 H), 6.85–6.89 (m, 4 H), 7.12 (m, 2 H), 7.47–7.49 (m, 6 H),
7.76 (dd, 1 H).
13C NMR (CDCl3): d = 25.3, 27.9, 29.0, 32.6, 33.7, 55.3, 67.7,
114.4, 114.6, 114.7, 121.8, 126.8, 127.6, 128.0, 129.9, 132.8, 138.4,
146.2, 149.7, 158.5, 161.6, 165.7.
MS (EI): m/z = 509.44.
Anal. Calcd for C28H29BrO4: C, 66.01; H, 5.74. Found: C, 65.78; H,
5.68.
Anal. Calcd for C21H23N3O5: C, 63.46; H, 5.83; N, 10.57. Found: C,
63.29; H, 5.76; N, 10.58.
4¢-Cyanobiphenyl-4-yl 4-{[6-(Acryloyloxy)hexyl]oxy}benzoate
(Entry 12)
This compound was prepared from 4-{[6-(acryloyloxy)hex-
yl]oxy}benzoic acid and 4¢-hydroxybiphenyl-4-carbonitrile using
CH2Cl2 as the solvent.
6-[(4¢-Cyanobiphenyl-4-yl)oxy]hexyl Acrylate (Entry 8)
This compound was prepared from acrylic acid and 4¢-[(6-hydroxy-
hexyl)oxy]biphenyl-4-carbonitrile using CH2Cl2 as the solvent.
Yield: 72% (<90 based on recovered alcohol component); white
solid; mp 70–71 °C.
1H NMR (CDCl3): d = 1.38–1.45 (m, 4 H), 1.60–1.80 (m, 4 H), 3.94
(t, 2 H, J = 6.4 Hz), 4.10 (t, 2 H, J = 6.6 Hz), 5.75 (dd, 1 H), 6.04
(dd, 1 H), 6.33 (dd, 1 H), 6.91 (d, 2 H, J = 6.8 Hz), 7.45 (d, 2 H,
J = 8.8 Hz), 7.53–7.63 (m, 4 H).
13C NMR (CDCl3): d = 25.6, 28.4, 29.0, 64.3, 67.8, 109.9, 114.9,
119.0, 126.9, 128.2, 128.4, 130.4, 131.2, 132.4, 145.1, 159.6, 166.2.
MS (FAB): m/z = 349.14 (M+).
Yield: 64% (<90 based on recovered alcohol component); colorless
solid; mp 110–111 °C.
1H NMR (CDCl3): d = 1.4–1.6 (m, 4 H), 1.69 (quint, 2 H, J = 7.5
Hz), 1.75 (quint, 2 H, J = 7.5 Hz), 3.99 (t, 2 H, J = 6.4 Hz), 4.11 (t,
2 H, J = 6.6 Hz), 5.74 (dd, 1 H), 6.07 (dd, 1 H), 6.33 (dd, 1 H), 6.90
(d, 2 H, J = 11.7 Hz), 7.25 (d, 2 H, J = 6.9 Hz), 7.53–7.68 (m, 6 H),
8.09 (d, 2 H, J = 11.6 Hz).
13C NMR (CDCl3): d = 25.6, 28.4, 28.9, 64.3, 68.0, 110.9, 114.2,
118.7, 121.2, 122.4, 127.6, 128.2, 128.4, 130.4, 132.2, 132.5, 136.6,
144.8, 151.5, 163.5, 164.7, 166.2.
Anal. Calcd for C22H23NO3: C, 75.62; H, 6.63; N, 4.01. Found: C,
75.38; H, 6.62; N, 4.01.
MS (FAB): m/z = 470.21 (M + H+).
Ferrocene Carboxylic Acid 11-Bromoundecyl Ester (Entry 9)
This compound was prepared from ferrocene carboxylic acid and
11-bromoundecan-1-ol using CH2Cl2 as the solvent.
Anal. Calcd for C29H27NO5: C, 74.18; H, 5.80; N, 2.98. Found: C,
73.93; H, 5.75; N, 2.96.
4¢-Hydroxybiphenyl-4-yl 3-(4-Methoxyphenyl)acrylate (Entry
13)
This compound was prepared from 3-(4-methoxyphenyl)acrylic
acid and biphenyl-4,4¢-diol using CH2Cl2 as the solvent.
Yield: 70%; orange solid; mp 51–52 °C (petroleum ether).
1H NMR (CDCl3): d = 1.10–1.45 (m, 18 H), 1.55–1.85 (m, 4 H),
3.28–3.41 (m, 2 H), 4.10–4.40 (m, 5 H), 4.75–4.85 (m, 2 H).
13C NMR (CDCl3): d = 26.0, 26.8, 28.1, 28.6, 28.8, 29.2, 29.3, 32.7,
33.9, 45.1, 64.2, 69.9, 70.3, 71.5, 71.8, 171.7.
MS (FAB): m/z = 463.9 (M + H+).
Yield: 42%; colorless crystals; mp 220–222 °C (EtOH).
1H NMR (DMSO-d6): d = 3.82 (s, 3 H), 6.73 (dd, 1 H), 6.85 (m 2
H), 7.05 (m, 2 H), 7.24 (m, 2 H), 7.48 (m, 2 H), 7.60 (m, 2 H), 7.79
(m, 2 H), 7.85 (dd, 1 H), 9.56 (s, 1 H).
13C NMR (DMSO-d6): d = 55.5, 114.4, 114.6, 115.8, 122.2, 126.6,
127.0, 127.8, 130.2, 130.6, 137.9, 146.4, 149.4, 157.2, 161.6.
Anal. Calcd for C22H31BrFeO2: C, 57.04; H, 6.75. Found: C, 57.40;
H, 6.89.
Ferrocene Carboxylic Acid 4-Cyclohexylphenyl Ester (Entry
10)
MS (EI): m/z = 346.38.
This compound was prepared from ferrocene carboxylic acid and 4-
cyclohexylphenol using CH2Cl2 as the solvent.
Anal. Calcd for C22H18O4: C, 76.29; H, 5.24. Found: C, 76.15; H,
5.17.
Yield: 78% (<90 based on recovered alcohol component); orange
solid; mp 120–121 °C (petroleum ether).
1H NMR (CDCl3): d = 1.30–1.40 (m, 5 H), 1.81–2.02 (m, 5 H),
2.45–2.54 (m, 1 H), 4.32–4.40 (m, 5 H), 4.40–4.52 (m, 2 H), 4.90–
5.10 (m, 2 H), 7.10–7.20 (m, 2 H), 7.30–7.40 (m, 2 H).
13C NMR (CDCl3): d = 26.0, 26.8, 34.4, 43.9, 70.0, 70.3, 70.7, 71.9,
121.2, 127.6, 145.2, 148.7, 170.3.
4¢-Hydroxybiphenyl-4-yl 3-(1,3-Benzodioxol-5-yl)acrylate (En-
try 14)
This compound was prepared from 3-(1,3-benzodioxol-5-yl)acrylic
acid and biphenyl-4,4¢-diol using THF as the solvent.
Yield: 38%; colorless crystals; mp 230–232 °C (EtOH).
1H NMR (DMSO-d6): d = 3.33 (s, 2 H), 6.75 (dd, 1 H), 6.86 (m, 1
H), 7.00 (m, 2 H), 7.25 (m, 2 H), 7.48 (m, 2 H), 7.58 (m, 2 H), 7.76
(m, 2 H), 7.81 (dd, 1 H), 9.55 (s, 1 H).
GC-MS: m/z = 388.
Anal. Calcd for C23H24FeO2: C, 71.15; H, 6.23. Found: C, 71.13; H,
6.23.
Synthesis 2004, No. 15, 2485–2492 © Thieme Stuttgart · New York