Isopropanol → 2-(benzyloxymethyl)-3,4-dihydro-2H-pyran

HRID 1045403

Reaktionsgleichung

Reaktionsgleichung von HRID 1045403
[CH2:1]([O:4][CH:5]([CH2:15][CH:16]=[CH2:17])[CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)C=C.C(O)(C)C.[OH-].[Na+]>C1(C)C=CC=CC=1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1.C1CCC([PH+](C2CCCCC2)C2CCCCC2)CC1.C1CCC([PH+](C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[CH2:8]([O:7][CH2:6][CH:5]1[CH2:15][CH2:16][CH:17]=[CH:1][O:4]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

7

Edukt 3

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 12996273((2-(Allyloxy)pent-4-enyloxy)methyl)benzene

Produkt 1

HCID 40956582-(benzyloxymethyl)-3,4-dihydro-2H-pyran

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6392641Grubbs CatalystKatalysatorHCID 11967259Benzylidenebis(tricyclohexylphosphine)dichlororutheniumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Benzylidene-bis(tricyclohexylphosphine)dichlororuthenium, bis(tricyclohexylphosphine) benzylidine ruthenium(IV) chloride—Grubbs 1 generation catalyst (0.5 g, 0.54 mmol) was added in one portion to a stirred solution of ((2-(allyloxy)pent-4-enyloxy)methyl)benzene (12) (4 g, 17.2 mmol) in toluene (200 mL). The resulting mixture was heated at 50° C. under N2 for 2 hours before isopropanol (18 mL) and NaOH (0.17 g) were added. The mixture was then heated at 120° C. overnight. The solvent was evaporated and the residue was purified over silica gel using Et2O and hexane to give 2-(benzyloxymethyl)-3,4-dihydro-2H-pyran (13).

Aufarbeitung

  1. additionwere added
  2. customThe solvent was evaporated
  3. customthe residue was purified over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4c0b433d4a6b4a059af057edae0e945c
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569283B2

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