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

HRID 357505

반응식

HRID 357505 반응식
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH:10]=[O:11].[CH2:12](O)[CH:13]=[CH:14][CH3:15].C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>>[CH2:12]([O:11][CH2:10][C:3]1[C:4]([O:8][CH3:9])=[N:5][CH:6]=[CH:7][C:2]=1[I:1])[CH:13]=[CH:14][CH3:15]

참가 물질

6

반응물 5

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 200242-Buten-1-olHCID 516892Sodium BicarbonateHCID 100383814-Iodo-2-methoxynicotinaldehyde

생성물 1

HCID 544155093-(But-2-enyloxymethyl)-4-iodo-2-methoxypyridine

반응 조건

온도
22 °C

실험 절차

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.

후처리

  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.)

출처 및 근거

ORD 기록
ord-4dc7f9f83eef4446be502cef9b65f8d1
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840898

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