Page 7 of 13
The Journal of Organic Chemistry
19F NMR (377 MHz, Chloroform-d) δ -62.7. HRMS
(10g, 61.7mmol), oxazolidinone 1 (16g, 185.1mmol)
and PTSA (1.18g, 6.17mmol) were refluxed in 100 ml
toluene to afford product 3a (4.53g, 32% yield).
(ESI-TOF) calcd for C15H16F3NO2Na [M+Na]+:
322.1035, found: 322.1025.
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(Z)-3-(1-(thiophen-2-yl)pent-1-en-1-yl)oxazolidin-2-one
(3f)
(Z)-3-(1-(3-methoxyphenyl)pent-1-en-1-yl)oxazolidin-2-
one (3b)
1
Brown oil, 0.332g (14% yield). H NMR (400 MHz,
1
Colorless oil, 0.548g (21% yield). H NMR (400 MHz,
Chloroform-d) δ 7.20 – 7.17 (m, 1H), 6.99 – 6.95 (m,
2H), 6.07 (t, J = 7.3 Hz, 1H), 4.53 – 4.47 (m, 2H), 3.82 –
3.76 (m, 2H), 2.17 (q, J = 7.4 Hz, 2H), 1.56 – 1.48 (m,
2H), 0.97 (t, J = 7.4 Hz, 3H). 13C{1H} NMR (101 MHz,
CDCl3) δ 156.2, 140.4, 130.3, 128.8, 127.6, 124.8,
123.7, 62.4, 46.0, 30.0, 22.0, 14.0. HRMS (ESI-TOF)
calcd for C12H15NO2SNa [M+Na]+: 260.0716, found:
260.0738.
Chloroform-d) δ 7.26 (d, J = 15.9 Hz, 1H), 6.93 (ddd, J
= 7.7, 1.7, 1.0 Hz, 1H), 6.88 – 6.86 (m, 1H), 6.84 (ddd, J
= 8.1, 2.6, 0.9 Hz, 1H), 6.01 (t, J = 7.2 Hz, 1H), 4.52 –
4.39 (m, 2H), 3.81 (s, 3H), 3.71 – 3.58 (m, 2H), 2.20 (q,
J = 7.3 Hz, 2H), 1.54 (q, J = 7.4 Hz, 2H), 0.98 (t, J = 7.4
Hz, 3H). 13C{1H} NMR (101 MHz, Chloroform-d) δ
160.1, 156.5, 137.6, 133.8, 130.9, 129.9, 118.6, 113.5,
112.0, 62.4, 55.5, 45.9, 30.5, 22.2, 14.2. HRMS (ESI-
TOF) calcd for C15H19NO3Na [M+Na]+: 284.1257,
found: 284.1256.
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(Z)-3-(1-(naphthalen-2-yl)pent-1-en-1-yl)oxazolidin-2-
one (3g)
Colorless oil, 0.562g (20% yield). 1H NMR (400 MHz,
Chloroform-d) δ 7.82 (dd, J = 8.9, 4.4 Hz, 3H), 7.75 (s,
1H), 7.55 – 7.42 (m, 3H), 6.15 (t, J = 7.2 Hz, 1H), 4.58 –
4.45 (m, 2H), 3.77 – 3.65 (m, 2H), 2.27 (q, J = 7.3 Hz,
2H), 1.59 (h, J = 7.3 Hz, 2H), 1.02 (t, J = 7.4 Hz, 3H).
13C{1H} NMR (101 MHz, CDCl3) δ 156.53, 133.91,
133.31, 133.24, 133.06, 131.14, 128.45, 128.10, 127.58,
126.43, 126.23, 124.78, 123.82, 62.27, 45.78, 30.40,
22.13, 14.06. HRMS (ESI-TOF) calcd for C18H19NO2Na
[M+Na]+: 304.1308, found: 304.1307.
(Z)-3-(1-(4-bromophenyl)pent-1-en-1-yl)oxazolidin-2-
one (3c)
1
Colorless oil, 0.556g (18% yield). H NMR (400 MHz,
Chloroform-d) δ 7.53 – 7.43 (m, 2H), 7.21 (d, J = 8.7
Hz, 2H), 6.01 (t, J = 7.2 Hz, 1H), 4.54 – 4.41 (m, 2H),
3.69 – 3.46 (m, 2H), 2.19 (q, J = 7.3 Hz, 2H), 1.54 (q, J
= 7.4 Hz, 2H), 0.98 (t, J = 7.4 Hz, 3H). 13C{1H} NMR
(101 MHz, Chloroform-d) δ 156.5, 135.1, 133.2, 132.0,
131.5, 127.6, 122.3, 62.4, 45.8, 30.5, 22.2, 14.2. HRMS
(ESI-TOF) calcd for C14H16BrNO2Na [M+Na]+:
332.0257, found: 332.0262.
(Z)-3-(3-methyl-1-phenylbut-1-en-1-yl)oxazolidin-2-one
(3h)
(Z)-3-(1-(4-fluorophenyl)pent-1-en-1-yl)oxazolidin-2-
one (3d)
1
Colorless oil, 0.693g (30% yield). H NMR (400 MHz,
1
Chloroform-d) δ 7.41 – 7.30 (m, 5H), 6.04 (t, J = 7.2 Hz,
1H), 4.55 – 4.42 (m, 2H), 3.73 – 3.65 (m, 2H), 2.24 (q, J
= 7.3 Hz, 2H), 1.65 – 1.54 (m, 2H), 1.01 (t, J = 7.4 Hz,
3H). 13C{1H} NMR (101 MHz, Chloroform-d) δ 156.5,
135.8, 133.9, 130.6, 128.7, 128.2, 125.9, 62.3, 45.7,
Colorless oil, 0.598g (24% yield). H NMR (400 MHz,
Chloroform-d) δ 7.37 – 7.30 (m, 2H), 7.13 – 6.98 (m,
2H), 5.96 (t, J = 7.2 Hz, 1H), 4.56 – 4.43 (m, 2H), 3.71 –
3.58 (m, 2H), 2.21 (q, J = 7.3 Hz, 2H), 1.65 – 1.48 (m,
2H), 1.00 (t, J = 7.4 Hz, 3H). 13C{1H} NMR (101 MHz,
Chloroform-d) δ 162.6 (d, J = 270.4 Hz) 156.43, 133.00,
132.07 (d, J = 3.3 Hz), 130.49 (d, J = 1.4Hz), 127.65,
127.57, 115.74, 115.52, 62.27, 45.67, 30.28, 22.08,
14.02. 19F NMR (377 MHz, Chloroform-d) δ -113.7.
HRMS (ESI-TOF) calcd for C14H16FNO2Na [M+Na]+:
272.1057, found: 272.1059.
30.3, 22.1, 14.1.
HRMS (ESI-TOF) calcd for
C14H17NO2Na [M+Na]+: 254.1151, found: 254.1151.
(Z)-3-(1-phenylbut-1-en-1-yl)oxazolidin-2-one (3i)
Colorless oil, 0.651g (30% yield). 1H NMR (400 MHz,
Chloroform-d) δ 7.37 – 7.30 (m, 4H), 7.31 – 7.28 (m,
1H), 5.98 (t, J = 7.2 Hz, 1H), 4.52 – 4.38 (m, 2H), 3.72 –
3.59 (m, 2H), 2.24 (p, J = 7.5 Hz, 2H), 1.12 (t, J = 7.5
Hz, 3H). 13C{1H} NMR (101 MHz, Chloroform-d) δ
156.7 , 135.9 , 133.4 , 132.3 , 128.8 , 128.3 , 126.0 , 62.4
, 45.8 , 21.8 , 13.6 . HRMS (ESI-TOF) calcd for
C13H15NO2Na [M+Na]+: 240.0995, found: 240.0987.
(Z)-3-(1-(4-(trifluoromethyl)phenyl)pent-1-en-1-
yl)oxazolidin-2-one (3e)
1
Colorless oil, 0.598g (20% yield). H NMR (400 MHz,
Chloroform-d) δ 7.61 (dt, J = 7.9, 0.8 Hz, 2H), 7.45 (dt,
J = 7.9, 0.8 Hz, 2H), 6.12 (t, J = 7.2 Hz, 1H), 4.56 – 4.42
(m, 2H), 3.73 – 3.58 (m, 2H), 2.24 (q, J = 7.4 Hz, 2H),
1.62 – 1.49 (m, 2H), 1.00 (t, J = 7.4 Hz, 3H). 13C{1H}
NMR (101 MHz, Chloroform-d) δ 156.5, 139.7, 133.3,
133.1, 130.3 (q, J = 32.5, 31.7 Hz), 126.2, 128.3 – 125.8
(m), 123.4 (q, J = 271.9 Hz), 62.4, 45.8, 30.6, 22.1, 14.2.
(Z)-3-(1,2-diphenylvinyl)oxazolidin-2-one (3j) 8b
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