Trifluoroacetic acid → 3-(But-2-enyloxymethyl)-4-iodo-2-methoxypyridine

温度

22 °C

A 500 mL 3-necked round-bottom flask is equipped with an overhead mechanical stirrer under nitrogen, the flask is charged with 4-iodo-2-methoxy-pyridine-3-carbaldehyde (75.0 g, 0.29 mol) prepared as in example 1, crotyl alcohol (75 mL, 0.88 mol), and triethylsilane (70 mL, 0.44 mol). To the stirred suspension at 0° C. is added trifluoroacetic acid (175 mL, 2.27 mol) dropwise via an addition funnel. The resulting solution is stirred at about 22° C. for approximately 12 hr. The reaction mixture is slowly poured into a rapidly stirring saturated sodium bicarbonate solution (2 L). The mixture is extracted with 3×500 mL of hexane. The combined organic layers are dried over sodium sulfate, filtered, and concentrated in vacuo to give an oil. Purification of this oil by vacuum distillation (about 0.4 mm Hg, about 120°-130° C.) yields 3-(but-2-enyloxymethyl)-4-iodo-2-methoxy-pyridine as a pale yellow oil: 1H-NMR (400 MHz, CDCl3) δ7.69 (d, J=5 Hz, 1H), 7.34 (d, J=5 Hz, 1H), 5.71 (m, 2H), 4.58 (s, 2H), 4.02 (d, J=1 Hz, 2H), 3.94 (s, 3H), 1.72 (d, J=6 Hz, 3H); IR (neat) 2948, 2859, 1561, 1459, 1381, 1361, 1301, 1233, 1169, 1094, 1052 cm-1 ; Elemental analysis: calculated for C11H14NO2I: C 41.40, H 4.42, N 4.39, I 39.76; Found: C 41.31, H 4.45, N 4.37, I39.71.

1. customA 500 mL 3-necked round-bottom flask is equipped with an overhead mechanical stirrer under nitrogen
2. extractionThe mixture is extracted with 3×500 mL of hexane
3. dry with materialThe combined organic layers are dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customto give an oil
7. customPurification of this oil
8. distillationby vacuum distillation (about 0.4 mm Hg, about 120°-130° C.)

ORDレコード

ord-4dc7f9f83eef4446be502cef9b65f8d1

出典データセット

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05840898