Triphenylphosphine → ethyl 3-methyl-5-(4-Boc-morpholin-2-ylmethoxy)-benzofuran-2-carboxylate

HRID 606583

Reaktionsgleichung

Reaktionsgleichung von HRID 606583
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:34][C:35]1[C:39]2[CH:40]=[C:41]([OH:44])[CH:42]=[CH:43][C:38]=2[O:37][C:36]=1[C:45]([O:47][CH2:48][CH3:49])=[O:46].[C:50]([N:57]1[CH2:62][CH2:61][O:60][CH2:59][CH:58]1C(O)=O)([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51]>ClCCl>[CH3:34][C:35]1[C:39]2[CH:40]=[C:41]([O:44][CH2:1][CH:59]3[O:60][CH2:61][CH2:62][N:57]([C:50]([O:52][C:53]([CH3:54])([CH3:55])[CH3:56])=[O:51])[CH2:58]3)[CH:42]=[CH:43][C:38]=2[O:37][C:36]=1[C:45]([O:47][CH2:48][CH3:49])=[O:46]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 27601334-(tert-Butoxycarbonyl)morpholine-3-carboxylic acidHCID 42883413Ethyl 5-hydroxy-3-methyl-1-benzofuran-2-carboxylate

Produkt 1

HCID 67046655ethyl 3-methyl-5-(4-Boc-morpholin-2-ylmethoxy)-benzofuran-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triphenyl phosphine polymer bound (1.37 mmol) was suspended in anhydrous dichloromethane (10 ml) then diisopropyl azodicarboxylate (1.18 mmol) was added and the mixture was stirred for 15 minutes at room temperature. Then ethyl 3-methyl-5-hydroxybenzofuran carboxylate (0.91 mmol) was added over 5 minutes followed by the addition of 4-N-boc-3-morpholinecarboxylic acid (0.91 mmol) over 5 minutes too. The mixture was stirred at room temperature over night. The solvent was evaporated under vacuo and the residue purified by flash chromatography to obtain ethyl 3-methyl-5-(4-Boc-morpholin-2-ylmethoxy)-benzofuran-2-carboxylate: m/z=419 in MS ES+, as clear oil.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature over night
  2. customThe solvent was evaporated under vacuo
  3. customthe residue purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-520abe56c59b4536864cbe3c2f122d97
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915300B2

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