Triphenylphosphine → methyl 3-(benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]benzoate

HRID 20579

Reaktionsgleichung

Reaktionsgleichung von HRID 20579
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][C:16]1[CH:17]=[C:18]([CH:23]=[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=1)[C:19]([O:21][CH3:22])=[O:20].[CH3:34][O:35][CH2:36][C@@H:37](O)[CH3:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:27]([O:26][C:24]1[CH:23]=[C:18]([CH:17]=[C:16]([O:15][C@H:37]([CH3:38])[CH2:36][O:35][CH3:34])[CH:25]=1)[C:19]([O:21][CH3:22])=[O:20])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 6993459(2S)-1-methoxypropan-2-olHCID 7472028Methyl 3-(benzyloxy)-5-hydroxybenzoate

Produkt 1

HCID 59127090methyl 3-(benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]benzoateAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

DIAD (4.6 g, 0.029 mol) was added dropwise to a solution of methyl 3-hydroxy-5-{[phenylmethyl]oxy}benzoate (6 g, 0.023 mol), (S)-(+)-1-methoxy-2-propanol (2.59 g, 0.029 mol) and triphenylphosphine (7.53 g, 0.029 mol) in THF (100 mL), under argon, at 0° C. The reaction was stirred at 0° C. for 1 hour and at RT for 20 hours. The volatiles were removed in vacuo and isohexane/ethyl acetate 2:1 added followed by stirring for 1 hour. A white solid was removed by filtration and the filtrate was evaporated to a residue which was chromatographed on silica, eluting with a gradient of 0-20% ethyl acetate in isohexane, to give the desired compound (5.11 g).

Aufarbeitung

  1. customThe volatiles were removed in vacuo and isohexane/ethyl acetate 2:1
  2. additionadded
  3. stirringby stirring for 1 hour
  4. customA white solid was removed by filtration
  5. customthe filtrate was evaporated to a residue which
  6. customwas chromatographed on silica
  7. washeluting with a gradient of 0-20% ethyl acetate in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-9842d4c846f34ce89bc694761081e379
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745475B2

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