2
430
Chen and Gabathuler
(
CH ), 18.9 (CH ), 30.5 (CH ), 34.9 (CH ), 61.5, 63.3, 65.8, 66.4, 70.5, 72.4,
2
3
2
2
þ
1
C, 56.39; H, 9.46. Found: C, 56.12; H, 9.22.
73 (COO) ppm. LC-MS, m/z ¼ 257 (M þ Na) . Anal. Calcd. for C H O ,
1
1 22 5
tert-Butyl 3-[2-(2-hydroxy-ethoxy)-ethoxy]-propanoate [6, C H O ,
7
1
1
22
FW ¼ 234]. Light yellow oil. Yield 79%. IR, n ¼ 3438, 2882, 1722, 1448,
21 1
341, 1177, 1122, 1077, 936, 888, 834, 815, 535 cm . H NMR (200 MHz,
1
CDCl ), d ¼ 1.39 (s, 9H, 3 CH ), 2.55 (t, J ¼ 7 Hz, 2H, CH ), 3.00 (brs, 1H,
3
3
2
1
OH), 3.80 (m, 8H, 4OCH ), 4.20 (m, 2H, CH O) ppm. C NMR (50 MHz,
3
2
2
CDCl ), d ¼ 29.0 (CH ), 30.5 (CH ), 34.9 (CH ), 63.3, 65.8, 70.5, 72.4,
3
3
2
2
þ
7
C H O , C, 56.39; H, 9.46. Found: C, 56.42; H, 9.52.
9.0, 173 (COO) ppm. LC-MS, m/z ¼ 257 (M þ Na) . Anal. Calcd. for
1
1 22 5
n-Butyl 3-[2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy]-propanoate [7,
C H O , FW ¼ 278]. Light yellow oil. Yield 89%. IR, n ¼ 3455, 2845,
1
3
26
6
21 1
734, 1456, 1345, 1178, 1124, 1056, 946, 867, 845, 822, 545 cm . H NMR
1
(
200 MHz, CDCl ), d ¼ 1.03 (t, J ¼ 7 Hz, 3H, CH ), 1.42 (m, 2H, CH ), 1.58
3
3
2
(
m, 2H, CH ), 2.55 (t, J ¼ 7 Hz, 2H, CH ), 3.20 (brs, 1H, OH), 3.83 (m, 14H,
2
2
1
3
7
OCH ), 4.22 (m, 2H, CH O) ppm. C NMR (50 MHz, CDCl ), d ¼ 13.7
2
2
3
(CH ), 18.6 (CH ), 30.4 (CH ), 34.7 (CH ), 62.5, 63.5, 65.4, 66.4 (multi-
3 2 2 2
þ
peaks), 72.5, 172.3 (COO) ppm. LC-MS, m/z ¼ 301 (M þ Na) . Anal.
Calcd. for C H O , C, 56.10; H, 9.42. Found: C, 56.42; H, 9.22.
1
3
26
6
tert-Butyl
3-[2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy]-propanoate
[
8, C H O , FW ¼ 278]. Light yellow oil. Yield 79%. IR, n ¼ 3438,
1
3
26
6
2
8
3
7
3
869, 1726, 1456, 1392, 1365, 1330, 1331, 1251, 1111, 1065, 943, 887,
2
1 1
46, 756, 547, 532, 505 cm . H NMR (200 MHz, CDCl ), d ¼ 1.41 (s, 9H,
3
CH ), 2.53 (t, J ¼ 7 Hz, 2H, CH ), 3.20 (brs, 1H, OH), 3.80 (m, 14H,
3
2
1
3
OCH ) ppm. C NMR (50 MHz, CDCl ), d ¼ 25.6 (CH ), 29.5 (CH ),
2
3
2
3
4.9 (CH ), 62.5, 65.5, 70.5 (multi-peaks), 72.5, 80.5 (OCMe ), 172.9
2
3
þ
(
COO) ppm. LC-MS, m/z ¼ 301 (M þ Na) . Anal. Calcd. for C H O , C,
1
3 26 6
5
6.10; H, 9.42. Found: C, 56.32; H, 9.32.
n-Butyl 3-f2-[2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy]-ethoxyg-pro-
panoate [9, C H O , FW ¼ 322]. Light yellow oil. Yield 84%. IR,
1
5
30
7
n ¼ 3433, 2853, 1728, 1457, 1337, 1182, 1133, 1044, 942, 865, 842, 834,
21 1
42 cm . H NMR (200 MHz, CDCl ), d ¼ 1.05 (t, J ¼ 7 Hz, 3H, CH ),
5
3
3
1
.45 (m, 2H, CH ), 1.62 (m, 2H, CH ), 2.45 (t, J ¼ 7 Hz, 2H, CH ), 3.15
2 2 2
1
3
(
brs, 1H, OH), 3.84 (m, 18H, 9OCH ), 4.27 (m, 2H, CH O) ppm. C NMR
2 2
(
50 MHz, CDCl ), d ¼ 14.2 (CH ), 18.4 (CH ), 30.2 (CH ), 34.1 (CH ),
3
3
2
2
2
6
1.5, 62.7, 64.8, 70.3 (multi-peaks), 72.5, 172.3 (COO) ppm. LC-MS,
þ
m/z ¼ 357 (M þ Na) . Anal. Calcd. for C H O , C, 55.88; H, 9.38.
1
5 30 7
Found: C, 55.65; H, 9.18.
tert-Butyl 3-f2-[2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy]-ethoxyg-pro-
panoate [10, C H O , FW ¼ 322]. Light yellow oil. Yield 87%. IR,
1
5
30
7
n ¼ 3450, 2870, 1726, 1451, 1365, 1329, 1249, 1105, 1068, 945, 887, 847,