Tributylphosphine → HCID 86583975, Verbindung

HRID 1270052Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1270052
[C:1]1([C:7]#[C:8]/[CH:9]=[CH:10]/[CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(P(CCCC)CCCC)CCC.[CH2:26]([O:28][C:29](=[O:42])[C@@H:30]([O:39][CH2:40][CH3:41])[CH2:31][C:32]1[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=1)[CH3:27].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1C=CC=CC=1>[CH2:26]([O:28][C:29](=[O:42])[C@@H:30]([O:39][CH2:40][CH3:41])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:12][CH2:11]/[CH:10]=[CH:9]/[C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:34][CH:33]=1)[CH3:27]

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 546319840317-08-6HCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate

Produkt 1

HCID 86583975HCID 86583975, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(E)-5-Phenyl-pent-2-en-4-yn-1-ol (328 mg, 2.07 mmol), tributylphosphine (606 mg, 3.0 mmol) and (S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (Tetrahedron Letters, Vol. 35, No. 19, 3139–3142, 1994) (495 mg, 2.07 mmol) were successively dissolved in dry benzene (30 mL) under a nitrogen atmosphere and the solution cooled to 0° C. Solid 1,1′-(azodicarbonyl) dipiperidine (756 mg, 3.0 mmol) was added, the mixture stirred for 10 min., then warmed to room temperature and stirred for 16 h. The reaction mixture was filtered and the filtrate concentrated in vacuo. The product was purified by flash column chromatography eluting with toluene graduated to toluene/ethyl acetate (19:1) to give 450 mg (57%) of the title compound.

Aufarbeitung

  1. temperaturewarmed to room temperature
  2. stirringstirred for 16 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe product was purified by flash column chromatography
  6. washeluting with toluene

Quellen und Nachweise

ORD-Eintrag
ord-5f93332082814bc89b8aee7a26890030
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202213B2

Notizen zur Reaktion

Wird geladen…