Triphenylphosphine → Methyl 4-(4-tetrahydropyranoyloxy)-2-methoxy-benzoate

HRID 1674

Reaktionsgleichung

Reaktionsgleichung von HRID 1674
[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.[O:33]1[CH2:38][CH2:37][CH:36](O)[CH2:35][CH2:34]1.N(C(OCC)=O)=N[C:42](OCC)=[O:43]>C1COCC1>[O:33]1[CH2:38][CH2:37][CH:36]([C:42]([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:43])[CH2:35][CH2:34]1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 12532676Methyl 4-hydroxy-2-methoxybenzoate

Produkt 1

HCID 57075614Methyl 4-(4-tetrahydropyranoyloxy)-2-methoxy-benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (713 mg, 3.92 mmol) in dry THF (7.5 mL) was added triphenylphosphine (1.42 g, 5.4 mmol) and the solution was cooled to 0° C. A 2.5 mL volume of tetrahydro-4H-pyran-4-ol (466 mL, 4.90 mmol) and diethyl azodicarboxylate (850 μL, 5.4 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 60:40 hexanes:EtOAc and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to afford methyl 4-(4-tetra-hydropyranoyloxy)-2-methoxy-benzoate.

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-2e02459c44114d51802676f652203008
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726172

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