Tributylphosphine → 2-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]thiazole

HRID 1096829

Reaktionsgleichung

Reaktionsgleichung von HRID 1096829
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[O:6][CH2:7][CH2:8][OH:9].[Cl:10][C:11]1[C:16](O)=[C:15]([Cl:18])[CH:14]=[C:13]([CH3:19])[CH:12]=1.P(CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1>[Cl:10][C:11]1[CH:12]=[C:13]([CH3:19])[CH:14]=[C:15]([Cl:18])[C:16]=1[O:9][CH2:8][CH2:7][O:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 13831TributylphosphineHCID 170772,6-Dichloro-4-methylphenolHCID 451219502-(Thiazol-2-yloxy)ethanol

Produkt 1

HCID 667835842-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]thiazoleAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 2-(thiazol-2-yloxy)ethanol (6.39 g, 44.0 mmol), 2,6-dichloro-p-cresol (15.6 g, 88.0 mmol), azodicarboxylic-dipiperidide (22.2 g, 88.0 mmol) and PBu3 (85%, 38.3 mL, 132 mmol) in toluene (325 mL) was heated to reflux for 30 min. The mixture was allowed to cool to rt, filtered, and the precipitate was washed thoroughly with toluene. The filtrate was evaporated under reduced pressure. The residue was diluted with EtOAc, and washed with aq. 1M NaOH (4×). The org. phase was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 1:19→1:9→1:4) yielded the title compound as a colourless solid (9.24 g, 69%). LC-MS: tR=1.06 min, ES+: 304.05.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 30 min
  3. filtrationfiltered
  4. washthe precipitate was washed thoroughly with toluene
  5. customThe filtrate was evaporated under reduced pressure
  6. additionThe residue was diluted with EtOAc
  7. washwashed with aq. 1M NaOH (4×)
  8. dry with materialphase was dried over MgSO4
  9. filtrationfiltered
  10. customthe solvents were removed under reduced pressure
  11. customPurification of the crude by FC (EtOAc/heptane 1:19→1:9→1:4)

Quellen und Nachweise

ORD-Eintrag
ord-bb51e01ccef1426a8f2a62160c0117c6
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138340B2

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