The Journal of Organic Chemistry
Note
967, 947, 841, 668, 609 cm−1. HRMS (ESI-TOF): m/z calculated for
C11H20O2Na [M + Na]+ 207.1361, found 207.1364.
mixture was purified by flash chromatography with 10% ethyl acetate
in hexanes as eluent to afford the product as a colorless oil in 68% yield
(146 mg). Rf = 0.3 (10% EtOAc in hexanes). H NMR (300 MHz,
1
(E)-2-(Pent-3-en-2-yl)isoindoline-1,3-dione (1). This com-
pound was prepared by the general procedure for the Mitsunobu
reaction.3 Analytical data are consistent with the literature.3
(E)-2-(Dec-2-en-1-yl)isoindoline-1,3-dione (8h). This com-
pound was prepared by the general procedure for the Mitsunobu
reaction using 1.56 g of (E)-dec-2-en-1-ol. The product was purified by
silica gel flash chromatography with 5% ethyl acetate in hexanes as
eluent to give the product as a colorless oil in 98% yield (2.80 g). Rf =
0.5 (5% EtOAc in hexanes). 1H NMR (500 MHz, CDCl3): δ 0.85 (t, J
= 7.0 Hz, 3H), 1.18−1.37 (m, 10H), 1.99 (q, J = 7.2 Hz 2H), 4.23 (d, J
= 6.0 Hz, 2H), 5.50 (dt, J = 15.5, 6.6 Hz, 1H), 5.74 (dt, J = 15.5, 7.1
Hz, 1H), 7.69−7.72 (m, 2H) 7.82−7.86 (m, 2H). 13C NMR (100
MHz, CDCl3): δ 14.3, 22.8, 29.1, 29.3, 32.0, 32.3, 39.8, 71.4, 123.2,
123.4, 132.4, 134.0, 135.6, 168.2. IR (neat): 2923, 2853, 1771, 1709,
1466, 1390, 1354, 1186, 1099, 966, 716 cm−1. HRMS (AP-TOF): m/z
calculated for C18H24NO2 [M + H]+ 286.1807, found 286.1802.
(Z)-Pent-2-en-1-yl Benzoate (8i). This compound was prepared
by the general procedure for benzoyl protection using 861 mg of (Z)-
pent-2-en-1-ol. The product was purified by silica gel flash
chromatography with 5% ethyl acetate in hexanes as eluent to give
the product as a colorless oil in 90% yield (1.71 g). Analytical data are
consistent with the literature.14
CDCl3): δ 0.88 (t, J = 6.8 Hz, 3H), 1.21−1.33 (m, 8H), 1.54−1.62 (m,
2H), 2.04 (s, 3H), 2.44 (t, J = 7.4 Hz, 2H), 2.74 (t, J = 6.3 Hz, 2H),
4.34 (t, J = 6.3 Hz, 2H). 13C NMR (100 MHz, CDCl3): δ 14.2, 21.0,
22.7, 23.7, 29.2, 29.3, 31.8, 41.3, 43.4, 59.6, 171.0, 208.2. IR (neat):
2926, 2855, 1739, 1715, 1366, 1233, 1036, 668 cm−1. HRMS (ESI-
TOF): m/z calculated for C12H22O3Na [M+Na]+ 237.1467, found
237.1469.
3-Oxodecyl Benzoate (Table 1, Entry 5; 9e). The general
procedure for the TBHP-mediated Wacker oxidation was followed
using 130 mg of (E)-dec-2-en-1-yl benzoate (0.5 mmol). The crude
mixture was purified by flash chromatography with 20% diethyl ether
in hexanes as eluent to afford the product as a colorless oil in 61% yield
(84 mg). Rf = 0.5 (20% Et2O in hexanes). 1H NMR (400 MHz,
CDCl3): δ 0.87 (t, J = 6.6 Hz, 3H), 1.20−1.32 (m, 8H), 1.57−1.64 (m,
2H), 2.47 (t, J = 7.4 Hz, 2H), 2.87 (t, J = 6.3 Hz, 2H), 4.60 (t, J = 6.3
Hz, 2H), 7.42 (t, J = 7.7 Hz, 2H), 7.55 (t, J = 7.6 Hz, 1H), 8.00 (d, J =
5.8 Hz, 2H). 13C NMR (100 MHz, CDCl3): δ 14.2, 22.7, 23.8,
29.2(2), 31.8, 41.5, 43.4, 60.1, 128.4, 129.7, 130.1, 133.1, 166.5, 208.1.
IR (neat): 2925, 2854, 1717, 1602, 1451, 1271, 1110, 964, 708, 686
cm−1. HRMS (ESI-TOF): m/z calculated for C17H24O3Na [M + Na]+
299.1623, found 299.1622.
(Z)-Hex-3-en-1-yl Benzoate (8j). This compound was prepared
by the general procedure for benzoyl protection using 1.00 g of (Z)-
hex-3-en-1-ol. The product was purified by silica gel flash
chromatography with 5% ethyl acetate in hexanes as eluent to give
the product as a colorless oil in 86% yield (1.76 g). Analytical data are
consistent with the literature.15
(E)-Hex-3-en-1-yl Benzoate (10). This compound was prepared
by the general procedure for benzoyl protection using 1.56 g of (E)-
dec-2-en-1-ol. The product was purified by silica gel flash
chromatography with 10% ethyl acetate in hexanes as eluent to give
the product as a colorless oil in 95% yield (1.94 g). Analytical data are
consistent with the literature.15
(((7R,8S)-8-((E)-But-2-en-1-yl)-3-methoxy-4,7-dimethyl-
4,4a,5,6,7,8-hexahydro-3H-isochromen-3-yl)oxy)-
triisopropylsilane (14). This compound was prepared according to
the literature procedure.8 Analytical data are consistent with the
literature.8
Octan-4-one (Table 1, Entry 1; 9a). The general procedure for
the TBHP-mediated Wacker oxidation was followed using 112 mg of
(E)-oct-4-ene (1.0 mmol). The crude mixture was purified by flash
chromatography with 5% ethyl acetate in hexanes as eluent to afford
the product as a colorless oil in 71% yield (91 mg). The spectral data
were in accordance with those of the known commercially available
compound.
1-(Methoxymethoxy)decan-3-one (Table 1, Entry 6; 9f). The
general procedure for the TBHP-mediated Wacker oxidation was
followed using 100 mg of (E)-1-(methoxymethoxy)dec-2-ene (0.5
mmol). The crude mixture was purified by flash chromatography with
10% diethyl ether in hexanes as eluent to afford the product as a
colorless oil in 93% yield (100 mg). Rf = 0.2 (10% Et2O in hexanes).
1H NMR (400 MHz, CDCl3): δ 0.88 (t, J = 6.5 Hz, 3H), 1.21−1.34
(m, 8H), 1.55−1.62 (m, 2H), 2.45 (t, J = 7.4 Hz, 2H), 2.68 (t, J = 6.1
Hz, 2H), 3.37 (s, 3H), 3.80 (t, J = 6.0 Hz, 2H) 4.60 (s, 2H). 13C NMR
(125 MHz, CDCl3): δ 14.3, 22.8, 23.8, 29.2, 29.3, 31.9, 42.8, 43.6,
55.4, 62.9, 96.7, 209.4. IR (neat): 3743, 2925, 2855, 1715, 1457, 1379,
1213, 1149, 1110, 1041, 918, 668 cm−1. HRMS (ESI-TOF): m/z
calculated for C12H24O3Na [M + Na]+ 239.1623, found 239.1624.
4-Oxononan-2-yl Acetate (Table 1, Entry 7; 9g). The general
procedure for the TBHP-mediated Wacker oxidation was followed
using 92 mg of (E)-non-3-en-2-yl acetate (0.5 mmol). The crude
mixture was purified by flash chromatography with dichloromethane as
eluent to afford the product as a colorless oil in 57% yield (57 mg). Rf
1
= 0.3 (DCM). H NMR (500 MHz, CDCl3): δ 0.88 (t, J = 6.8 Hz,
3H), 1.20−1.34 (m, 7H), 1.52−1.60 (m, 2H), 2.00 (s, 3H), 2.40 (t, J =
7.3 Hz, 2H), 2.52 (dd, J = 16.2, 5.8 Hz, 1H), 2.76 (dd, J = 16.3, 7.0 Hz,
1H), 5.27 (sext., J = 6.3 Hz, 1H). 13C NMR (100 MHz, CDCl3): δ
14.1, 20.3, 21.4, 22.6, 23.5, 31.5, 43.6, 48.7, 67.4, 170.5, 208.1. IR
(neat): 2956, 2932, 2872, 1736, 1714, 1457, 1370, 1236, 1141, 1037,
956, 668, 607 cm−1. HRMS (ESI-TOF): m/z calculated for
C11H20O3Na [M + Na]+ 223.1310, found 223.1305.
2-(4-Oxopentan-2-yl)isoindoline-1,3-dione (Table 1, Entry 8;
2). The general procedure for the TBHP-mediated Wacker oxidation
was followed using 430 mg of (E)-2-(pent-3-en-2-yl)isoindoline-1,3-
dione (2.0 mmol). The crude mixture was purified by flash
chromatography with 15% ethyl acetate in hexanes as eluent to afford
the product as a colorless oil in 66% yield (305 mg). The spectral data
were in accordance with the previous report.3
Cyclododecanone (Table 1, Entry 2; 9b). The general
procedure for the TBHP-mediated Wacker oxidation was followed
using 166 mg of cyclododecene (1.0 mmol). The crude mixture was
purified by flash chromatography with 5% ethyl acetate in hexanes as
eluent to afford the product as a white solid in 76% yield (138 mg).
The spectral data were in accordance with those of the known
commercially available compound.
1-Hydroxydecan-3-one (Table 1, Entry 3; 9c). The general
procedure for the TBHP-mediated Wacker oxidation was followed
using 78 mg of (E)-dec-2-en-1-ol (0.5 mmol). The crude mixture was
purified by flash chromatography with 40% ethyl acetate in hexanes as
eluent to afford the product as a colorless oil in 32% yield (55 mg). Rf
2-(3-Oxodecyl)isoindoline-1,3-dione (Table 1, Entry 9; 9h).
The general procedure for the TBHP-mediated Wacker oxidation was
followed using 258 mg of (E)-2-(dec-2-en-1-yl)isoindoline-1,3-dione
(1.0 mmol). The crude mixture was purified by flash chromatography
with 10% ethyl acetate in hexanes as eluent to afford the product as a
white solid in 79% yield (237 mg). Rf = 0.3 (10% EtOAc in hexanes).
1
= 0.5 (40% EtOAc in hexanes). H NMR (500 MHz, CDCl3): δ 0.88
(t, J = 7.0 Hz, 3H), 1.22−1.34 (m, 8H), 1.59 (quint, J = 7.3 Hz, 2H),
2.44 (t, J = 7.5 Hz, 2H), 2.67 (t, J = 5.3 Hz, 2H), 3.85 (t, J = 5.3 Hz,
2H). 13C NMR (100 MHz, CDCl3): δ 14.3, 22.8, 23.9, 29.3, 29.4, 31.9,
43.6, 44.5, 58.2, 212.3. IR (neat): 3420, 2924, 2854, 1701, 1457, 1375,
1047, 668 cm−1. HRMS (ESI-TOF): m/z calculated for C10H20O2Na
[M + Na]+ 195.1361, found 195.1361.
3-Oxodecyl Acetate (Table 1, Entry 4; 9d). The general
procedure for the TBHP-mediated Wacker oxidation was followed
using 198 mg of (E)-dec-2-en-1-yl acetate (1.0 mmol). The crude
1
Mp: 88−90 °C. H NMR (400 MHz, CDCl3): δ 0.87 (t, J = 6.9 Hz,
3H), 1.19−1.31 (m, 8H), 1.56 (quint, J = 7.3, 2H), 2.41 (t, J = 7.6 Hz,
2H), 2.84 (t, J = 7.6 Hz, 2H), 3.96 (t, J = 7.4 Hz, 2H), 7.71 (dd, J =
5.5, 3.0 Hz, 2H), 7.83 (dd, J = 5.3, 3.1 Hz, 2H). 13C NMR (100 MHz,
CDCl3): δ 14.3, 22.8, 23.9, 29.3, 29.4, 31.9, 33.3, 40.8, 43.2, 123.5,
132.3, 134.2, 168.4, 208.5. IR (neat): 2923, 2853, 1704, 1652, 1436,
1685
dx.doi.org/10.1021/jo302638v | J. Org. Chem. 2013, 78, 1682−1686