1-Octanol → Octyl4'-methoxycarbonyloxy-4-biphenylcarboxylate

HRID 442579

Reaktionsgleichung

Reaktionsgleichung von HRID 442579
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][O:21][C:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([OH:39])=[O:38])=[CH:33][CH:32]=2)=[CH:27][CH:26]=1)=[O:23].[CH2:40](O)[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:40]([O:38][C:37]([C:34]1[CH:35]=[CH:36][C:31]([C:28]2[CH:27]=[CH:26][C:25]([O:24][C:22]([O:21][CH3:20])=[O:23])=[CH:30][CH:29]=2)=[CH:32][CH:33]=1)=[O:39])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]

Komponenten

6

Edukt 4

HCID 9571-OctanolHCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 183284084'-Methoxycarbonyloxy-4-biphenylcarboxylic acid2×

Produkt 1

HCID 18328376Octyl4'-methoxycarbonyloxy-4-biphenylcarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of triphenylphosphine (3.78 g, 0.014 mol) in dry tetrahydrofuran (50 ml) was added to a stirred solution of compound 4 (3.92 g, 0.014 mol), octan-1-ol (1.88 g, 0.014 mol) and diethyl azodicarboxylate (DEAD) (2.51 g, 0.014 mol) in dry tetrahydrofuran (100 ml) under an atmosphere of dry nitrogen. The addition was such that the triphenylphosphine was added over 30 seconds in which time the solution became hot and the white solid (4) and orange colour (DEAD) disappeared. The resultant solution was stirred overnight, the solvent was removed in vacuo and the viscous, oily residue was purified by column chromatography (10% petrol/dichloromethane) to give a colourless solid which was recrystallised from ethanol to leave colourless plates.

Aufarbeitung

  1. additionThe addition
  2. additionwas added over 30 seconds in which time the solution
  3. customthe solvent was removed in vacuo
  4. customthe viscous, oily residue was purified by column chromatography (10% petrol/dichloromethane)
  5. customto give a colourless solid which
  6. customwas recrystallised from ethanol
  7. customto leave colourless plates

Quellen und Nachweise

ORD-Eintrag
ord-84ebbcc068df4f88a51e1edae094ac0a
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891358

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