Triphenylphosphine → Methyl 4-(cis-2-phenyl-1-cyclohexanoyloxy)-2-methoxybenzoate

HRID 1677

Reaktionsgleichung

Reaktionsgleichung von HRID 1677
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:33]1([C@@H:39]2[CH2:44][CH2:43][CH2:42][CH2:41][C@H:40]2O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.N(C(OCC)=O)=N[C:48](OCC)=[O:49]>C1COCC1>[C:33]1([C@H:39]2[CH2:44][CH2:43][CH2:42][CH2:41][C@H:40]2[C:48]([O:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=2)=[O:49])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 102793rel-(1R,2S)-2-PhenylcyclohexanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 12532676Methyl 4-hydroxy-2-methoxybenzoate

Produkt 1

HCID 22883080Methyl 4-(cis-2-phenyl-1-cyclohexanoyloxy)-2-methoxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (310 mg, 1.7 mmol) in dry THF (1.25 mL) was added triphenylphosphine (446 mg, 1.7 mmol) and the solution was cooled to 0° C. A 500 mL volume of trans-2-phenyl-1-cyclohexanol (200 mg, 1.35 mmol) and diethyl azodicarboxylate (319 μL, 2.02 mmol) in THF was added dropwise via addition funnel over 0.5 h. The reaction was filtered and the solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column packed in 92:8 hexanes:EtOAc and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to afford methyl 4-(cis-2-phenyl-1-cyclohexanoyloxy)-2-methoxybenzoate.

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was chromatographed on a silica gel column
  4. washEtOAc and eluted with same
  5. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e05a7f6ef00b40218847ea8339f5616a
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726172

Verknüpfte Notizen

Wird geladen…