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4-Hydroxybiphenyl → 4-(Biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester

HRID 460041
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 460041
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([CH3:12])=[C:8]([CH2:10][OH:11])[CH:9]=1)=[O:4].O[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([CH3:12])=[C:8]([CH2:10][O:11][C:23]2[CH:24]=[CH:25][C:20]([C:17]3[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=3)=[CH:21][CH:22]=2)[CH:9]=1)=[O:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 71034-Hydroxybiphenyl2×HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 58824163Methyl 4-(hydroxymethyl)-5-methylfuran-2-carboxylate

Produkt 1

HCID 588241734-(Biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 4-hydroxymethyl-5-methyl-furan-2-carboxylic acid methyl ester (16) (1 g) in anhydrous tetrahydrofuran (20 mL) was cooled to 0° C. under a nitrogen atmosphere. 4-Hydroxybiphenyl (3 g) and triphenylphosphine (4.61 g) were added and the mixture was treated with diisopropylazodicarboxylate (3.46 mL) dropwise. The mixture was stirred at 0° C. for 10 min then cooling was removed and the mixture stirred for a further 3 hours. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate (50 mL) and water (100 mL). The organic phase was separated, dried and evaporated. The residue was purified by flash chromatography, eluting with pentane/ethyl acetate 9:1 by volume to give a mixture of the title compound and 4-hydroxybiphenyl (1.8 g). This material was purified further by flash chromatography eluting with dichloromethane/methanol 99:1 by volume to give compound 17 as a white solid (200 mg). LCMS System A: Rt=4.2 mins.

Aufarbeitung

  1. temperaturethen cooling
  2. customwas removed
  3. stirringthe mixture stirred for a further 3 hours
  4. customThe solvent was removed in vacuo
  5. customthe residue was partitioned between ethyl acetate (50 mL) and water (100 mL)
  6. customThe organic phase was separated
  7. customdried
  8. customevaporated
  9. customThe residue was purified by flash chromatography
  10. washeluting with pentane/ethyl acetate 9:1 by volume
  11. customto give

Quellen und Nachweise

ORD-Eintrag
ord-5cf0d657dc5c41859c28dcb3b9fdf2ad
Quelldatensatz
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07196089B2

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