t-Butyl bromide → ethyl 2-(tert-butoxy)-2-(1-methyl-3-phenyl-1H-indol-2-yl)acetate

HRID 590955

Reaktionsgleichung

Reaktionsgleichung von HRID 590955
[OH:1][CH:2]([C:8]1[N:9]([CH3:23])[C:10]2[C:15]([C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:24](Br)([CH3:27])([CH3:26])[CH3:25]>C1CCCCC1.[Ag-]=O>[C:24]([O:1][CH:2]([C:8]1[N:9]([CH3:23])[C:10]2[C:15]([C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])([CH3:27])([CH3:26])[CH3:25]

Komponenten

5

Edukt 2

HCID 10485t-Butyl bromideHCID 70813741ethyl 2-hydroxy-2-(1-methyl-3-phenyl-1H-indol-2-yl)acetate

Produkt 1

HCID 70813680ethyl 2-(tert-butoxy)-2-(1-methyl-3-phenyl-1H-indol-2-yl)acetateAusbeute 10,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418778HCID 178418778, VerbindungKatalysatorHCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-hydroxy-2-(1-methyl-3-phenyl-1H-indol-2-yl)acetate (1c) (300 mg, 0.97 mmol), silver (I) oxide (674 mg, 2.91 mmol) and tert-butylbromide (544 μL, 4.85 mmol) in cyclohexane (10 mL) was vigorously stirred for 2 hours under a nitrogen atmosphere. The reaction mixture was then filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired ether oxide (1d) as a white solid (35 mg, 0.1 mmol, 10%).

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10)

Quellen und Nachweise

ORD-Eintrag
ord-787cbc9ef451464693d9d65ae13616ee
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238026B2

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