StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Tetrahydrofuran → morpholine 5-(2-Benzyloxyphenyl)-3-oxo-pent-4-ynamide

HRID 1463925
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1463925
[C:1]([N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].C(O[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:24]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=O)C#C.[O:38]1CC[CH2:40][CH2:39]1>O>[NH:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[CH2:31]([O:30][C:24]1[CH:23]=[CH:28][CH:27]=[CH:26][C:25]=1[C:29]#[C:40][C:39](=[O:38])[CH2:2][C:1]([NH2:4])=[O:3])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 155434-AcetylmorpholineHCID 2724682Lithium diisopropylamideHCID 54058410Methyl-2-benzyloxyphenyl propiolate

Produkt 1

HCID 86747286morpholine 5-(2-Benzyloxyphenyl)-3-oxo-pent-4-ynamideAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Acetyl morpholine (546 ul, 4.72 mmole) was dissolved in 10 ml dry tetrahydrofuran in an oven dried 50 ml two neck round bottom flask under nitrogen. The solution was cooled to 0° C. and was treated slowly dropwise with lithium diisopropylamide (3.2 ml, 4.72 mmole). The mixture was stirred 30 minutes at 0° C. and was treated with methyl-2-benzyloxyphenyl propiolate (600 mg, 2.25 mmole) in 2 ml dry tetrahydrofuran. The reaction mixture was stirred for 1 hour at 0° C. and was diluted with 10 ml water. The volatiles were removed in vacuo and the residue was crystallized from diethyl ether/methanol (20:1). The tan solid was collected, was washed with diethyl ether, and was dried to afford 500 mg (61%) of morpholine-5-(2-Benzyloxyphenyl)-3-oxo-pent-4-ynamide as a tan solid. Melting Point: 224°-227° C.

Aufarbeitung

  1. dry with materialdried 50 ml two neck round bottom flask under nitrogen
  2. stirringThe reaction mixture was stirred for 1 hour at 0° C.
  3. customThe volatiles were removed in vacuo
  4. customthe residue was crystallized from diethyl ether/methanol (20:1)
  5. customThe tan solid was collected
  6. washwas washed with diethyl ether
  7. customwas dried

Quellen und Nachweise

ORD-Eintrag
ord-c351075d065040a1ba1d312e4d965ae0
Quelldatensatz
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05302613

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion