Triethylamine → HCID 22452629, Verbindung

HRID 2185881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2185881
[I:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:12]([NH2:14])=O)[C:3]=1[O:15][CH3:16].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[C:12]([C:4]1[C:3]([O:15][CH3:16])=[C:2]([I:1])[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=1)#[N:14]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 22452681HCID 22452681, Verbindung

Produkt 1

HCID 22452629HCID 22452629, VerbindungAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred, cooled (0° C.) suspension of 4-iodo-3-methoxy-5,6,7,8-tetrahydro-2-naphthalenecarboxamide (2.06 g, 6.22 mmol), triethylamine (2.77 mL, 19.91 mmol), and THF (40 mL) was added trifluoroacetic anhydride (1.23 mL, 8.71 mmol) dropwise via syringe. After addition, the ice bath was removed and the reaction stirred overnight at ambient temperature. The mixture was cooled to 0° C. and excess trifluoroacetic anhydride destroyed with H2O (2 mL). Ethyl acetate (50 mL) was added and the organic layer was washed with H2O (3×25 mL) and brine (25 mL), dried (NaSO4), filtered, concentrated in vacuo and purified by chromatography (100% DCM) to afford a light brown solid (1.96 g, 100%). 1H NMR (CDCl3) δ 7.29 (s, 1H), 4.0 (s, 3H), 2.74 (m, 4H), 1.76 (m, 4H), MS m/z 314 (M+H).

Aufarbeitung

  1. temperatureTo a stirred, cooled
  2. additionAfter addition
  3. customthe ice bath was removed
  4. temperatureThe mixture was cooled to 0° C.
  5. customexcess trifluoroacetic anhydride destroyed with H2O (2 mL)
  6. additionEthyl acetate (50 mL) was added
  7. washthe organic layer was washed with H2O (3×25 mL) and brine (25 mL)
  8. dry with materialdried (NaSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. custompurified by chromatography (100% DCM)

Quellen und Nachweise

ORD-Eintrag
ord-2f04be89c25841d884870ddf74d9735d
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06403601B1

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