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

Potassium Hydroxide → Tert-butyl 3-(3-bromophenyl)-3-(2-ethoxy-2-oxoethyl)azetidine-1-carboxylate

HRID 384062
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 384062
[OH-].[K+].[Br:3][C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1.[CH2:13]([O:15][C:16](=[O:29])[CH:17]=[C:18]1[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19]1)[CH3:14]>O1CCOCC1.[Cl-].[Na+].O>[Br:3][C:4]1[CH:5]=[C:6]([C:18]2([CH2:17][C:16]([O:15][CH2:13][CH3:14])=[O:29])[CH2:19][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21]2)[CH:7]=[CH:8][CH:9]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 2734318(3-Bromophenyl)boronic acidHCID 44195530tert-Butyl 3-(2-ethoxy-2-oxoethylidene)azetidine-1-carboxylate

Produkt 1

HCID 57969607Tert-butyl 3-(3-bromophenyl)-3-(2-ethoxy-2-oxoethyl)azetidine-1-carboxylateAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 31275
1,4-Dioxane
Lösungsmittel
2×
HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of [RhCl(COD)]2 (63 mg, 0.031 mmol) in dioxane (10 mL) was added aqueous KOH (1.5M, 8.29 mmol, 5.53 mL), followed by (3-bromophenyl)boronic acid (1.67 g, 8.29 mmol). Then a solution of the tert-butyl 3-(2-ethoxy-2-oxoethylidene)azetidine-1-carboxylate in dioxane (7.5 mL) was added. The reaction mixture was microwaved at 100° C. for 5 min at 300 W. Brine was added and the mixture was extracted twice with ethyl acetate. The combined organics were washed with brine and then dried (MgSO4), filtered and concentrated. Purification by column chromatography (4/1 Pet ether/ethyl acetate) gave the Michael adduct (1.31 g, 79%) as a light yellow oil.

Aufarbeitung

  1. customThe reaction mixture was microwaved at 100° C. for 5 min at 300 W
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography (4/1 Pet ether/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-bf62d6c7c30f48cfb84a527de268c497
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08367697B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion