Sodium Formate → Tert-butyl (5-formyl-2-methoxybenzyl)carbamate

HRID 1296217

Reaktionsgleichung

Reaktionsgleichung von HRID 1296217
Br[C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([CH:16]=1)[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[CH:19]([O-])=[O:20].[Na+]>CN(C)C=O.[C]=O.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:19]([C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([CH:16]=1)[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:20]

Komponenten

8

Edukt 2

HCID 2723810Sodium FormateHCID 22926030Tert-butyl (5-bromo-2-methoxybenzyl)carbamate

Produkt 1

HCID 22493931Tert-butyl (5-formyl-2-methoxybenzyl)carbamateAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 11776TriphenylphosphineKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 178418416HCID 178418416, VerbindungLösungsmittel

Versuchsvorschrift

1.015 g of t-butyl N-(5-bromo-2-methoxybenzyl)carbamate, 45 mg of dichlorobis(triphenylphosphine)palladium (II), 330 mg of sodium formate and 17 mg of triphenylphosphine were dissolved in anhydrous N,N-dimethylformamide, followed by stirring for 2 hours at 110° C. in carbon monoxide atmosphere. The reaction mixture was diluted with ethyl acetate, and washed with water and saturated sodium bicarbonate water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography, and 640 mg of t-butyl N-(5-formyl-2-methoxybenzyl)carbamate was obtained from fractions eluted with hexane-ethyl acetate (3:1).

Aufarbeitung

  1. washwashed with water and saturated sodium bicarbonate water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-04a0c5bca7cd4ea2a1e72ff93846ae5a
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244861B2

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