Tributylphosphine → Ethyl[2-methyl-4-(2-thien-2-ylethoxy)phenoxy]acetate

HRID 9653

Reaktionsgleichung

Reaktionsgleichung von HRID 9653
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[CH3:14])[CH3:2].[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH2:21][CH2:22]O.C(P(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:22][CH2:21][C:17]2[S:16][CH:20]=[CH:19][CH:18]=2)=[CH:9][C:8]=1[CH3:14])[CH3:2]

Komponenten

5

Edukt 3

HCID 13831TributylphosphineHCID 794002-ThiopheneethanolHCID 21986458Ethyl (4-hydroxy-2-methylphenoxy)acetate2×

Produkt 1

HCID 21986308Ethyl[2-methyl-4-(2-thien-2-ylethoxy)phenoxy]acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of ethyl(4-hydroxy-2-methylphenoxy)acetate (intermediate 7, 1.05 g) and 2-(2-thienyl)ethanol (0.64 g) in dry tetrahydrofuran was treated with tri-n-butyl phosphine (1.2 g) and azodicarbonyldimorpholide (1.53 g) and the mixture stirred at ambient temperature for 3 days. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and water. The organic layer was collected, dried over sodium sulfate, concentrated and the residue purified by SPE (Si cartridge) eluting with cyclohexane:ethyl acetate (20:1) to give the title compound as a colourless oil.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe organic layer was collected
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customthe residue purified by SPE (Si cartridge)
  7. washeluting with cyclohexane:ethyl acetate (20:1)

Quellen und Nachweise

ORD-Eintrag
ord-ae8f35505a5f42f7845c7a23a233be40
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091237B2

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