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

Acetic Acid → HCID 54508268, Verbindung

HRID 616859
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 616859
[N+:1]([CH2:4][CH:5]1[CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH:7]([CH2:14][CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:6]1[CH:23]=[CH:24][C:25](=[O:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([O-:3])=[O:2].[CH3:32][Mg]Br.[Cl-].[NH4+].C(O)(=O)C>O1CCCC1>[N+:1]([CH2:4][CH:5]1[CH2:13][C:8]2([O:9][CH2:10][CH2:11][O:12]2)[CH:7]([CH2:14][CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:6]1[CH:23]=[CH:24][C:25]([CH3:32])([OH:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([O-:3])=[O:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 70607475HCID 70607475, VerbindungHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 54508268HCID 54508268, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

A solution of 1.72 g. of 7-[8-nitromethyl-7-(3-oxo-1-octenyl)-1,4-dioxaspiro[4.4]non-6-yl]-5-heptenoic acid in 80 ml. of tetrahydrofuran was treated at -10° C. with 9.7 ml. of 3M methyl magnesium bromide in tetrahydrofuran and was stirred at 0° C. for one hour. The reaction mixture was added to aqueous ammonium chloride solution, acidified with acetic acid and extracted with ether. After washing with water and drying over magnesium sulfate, the extract was evaporated and the residue chromatographed on silica. Elution with 30% ethyl acetate in hexane gave 0.26 g. of the title product as an oil, λmaxfilm 3.00 (shoulder), 3.45, 5.80 (shoulder), 5.85, 6.45, 7.25, 10.30 μ. NMR: δ 1.32 (S, 15-methyl), 4.01 (S, 4, ketal), 4.40 (M, 2, CH2NO2), 5.22 (M, 2, 5 and 6--H), 5.63 (M, 2, 13 and 14--H) ppm. Mass spectrum: M+ at m/e 453), (theory 453), M+ --H2O at m/e 435.2571 (theory 435.2620).

Aufarbeitung

  1. extractionextracted with ether
  2. washAfter washing with water
  3. dry with materialdrying over magnesium sulfate
  4. customthe extract was evaporated
  5. customthe residue chromatographed on silica
  6. washElution with 30% ethyl acetate in hexane
  7. customgave 0.26 g

Quellen und Nachweise

ORD-Eintrag
ord-9290cd2735eb430b8d6e06ad2159d748
Quelldatensatz
uspto-grants-1978_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04076730

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion