Sodium Iodide → HCID 66869667, Verbindung

HRID 57216

Reaktionsgleichung

Reaktionsgleichung von HRID 57216
[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:24][CH2:25][CH2:26]Cl)=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[NH:28]1[CH2:33][CH2:32]O[CH2:30][CH2:29]1.[I-].[Na+].[CH3:36]N(C)C=O>>[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:24][CH2:25][CH2:26][N:28]2[CH2:33][CH2:32][CH2:36][CH2:30][CH2:29]2)=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Komponenten

5

Edukt 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 8083MorpholineHCID 668698443-Chloropropyl 5-(tetradecyloxy)furan-2-carboxylate

Produkt 1

HCID 66869667HCID 66869667, Verbindung

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a solution of the above prepared 3-chloropropyl 5-(tetradecyloxy)furan-2-carboxylate (0.272 g, 0.68 mmol) in 6 mL of N,N-dimethylformamide was added morpholine (0.535 mL, 6.1 mmol) and sodium iodide (10 mg). The resulting solution was stirred at 55° C. for 36 hrs at which time HPLC analysis of the reaction mixture indicated near complete consumption of the starting material. The solution was diluted with EtOAc (30 mL), brine (10 mL) and water (10 mL) such that both phases were clear solutions. The phases were separated and the organic phase was washed with water (20 mL) and brine (20 mL) and then dried and concentrated. The crude material was purified by flash chromatography eluting with 5-40% EtOAc in hexanes to yield 0.217 g of the title compound. 1H NMR (300 MHz, CDCl3) δ: 7.10 (d, 1H), 5.30 (d, 1H), 4.30 (t, 2H), 4.10 (t, 2H), 3.7 (t, 4H), 2.40-2.50 (m, 6H), 1.90 (p, 2H), 1.76 (p, 2H), 1.18-1.50 (m, 22H), 0.89 (t, 3H).

Aufarbeitung

  1. customindicated near complete consumption of the starting material
  2. additionThe solution was diluted with EtOAc (30 mL), brine (10 mL) and water (10 mL) such that both phases
  3. customThe phases were separated
  4. washthe organic phase was washed with water (20 mL) and brine (20 mL)
  5. customdried
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography
  8. washeluting with 5-40% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-2287f33b86d64e2ea5c6e6f595650d9b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434718B2

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