Triethylamine → 1-(4-methoxyphenyl)-N-(1,1,1-trifluoropropan-2-ylidene)methanamine

HRID 887878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 887878
[F:1][C:2]([F:7])([F:6])[C:3](=O)[CH3:4].[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1.C(N(CC)CC)C>C(OCC)C.CCCCCC.Cl[Ti](Cl)(Cl)Cl>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:15]=[C:3]([CH3:4])[C:2]([F:7])([F:6])[F:1])=[CH:12][CH:11]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 9871Methyl trifluoromethyl ketoneHCID 754524-Methoxybenzylamine

Produkt 1

HCID 866576701-(4-methoxyphenyl)-N-(1,1,1-trifluoropropan-2-ylidene)methanamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24193Titanium TetrachlorideKatalysatorHCID 3283Diethyl EtherLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a stirring solution of trifluoroacetone (7.75 g, 69.2 mmol) in diethyl ether (60 ml) at −40° C. was added 4-methoxybenzyl amine (9.49 g, 69.2 mmol) and triethylamine (14 g, 138 mmol) in diethyl ether (40 ml). A cooled (0° C.) mixture of TiCl4 (6.56 g, 34.6 mmol) in hexane (40 ml) at was added dropwise over 10 minutes and the resulting mixture was allowed to warm up to ambient temperature over 20 mins and stirred at 50° C. for 2.5 h. The inorganic precipitate was removed by filtration and washed with diethyl ether. The filtrate was concentrated in vacuo to afford a yellow oil. Purification of the crude product by chromatography on silica eluting with 0% to 25% EtOAc in iso-hexane afforded the title product.

Aufarbeitung

  1. temperatureA cooled
  2. additionat was added dropwise over 10 minutes
  3. customThe inorganic precipitate was removed by filtration
  4. washwashed with diethyl ether
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto afford a yellow oil
  7. customPurification of the crude product by chromatography on silica eluting with 0% to 25% EtOAc in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-78dbb196ca834d27968967dde79ec022
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247436B2

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