Imidazole → 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)isobenzofuran-1(3H)-one

HRID 627800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627800
[OH:1][CH2:2][CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[O:5]1.[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16].N1C=CN=C1>C1COCC1>[Si:18]([O:1][CH2:2][CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[O:5]1)([C:15]([CH3:17])([CH3:16])[CH3:14])([CH3:20])[CH3:19]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 222749702-(3-Phthalidyl)ethanol

Produkt 1

HCID 711436383-(2-((tert-butyldimethylsilyl)oxy)ethyl)isobenzofuran-1(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-(2-hydroxyethyl)-3H-isobenzofuran-1-one (1.03 g, 5.781 mmol) dissolved in THF (10 mL) under N2 and TBDMSCl (958.4 mg, 6.359 mmol) then imidazole (472.3 mg, 6.937 mmol) added at RT. Reaction mixture stirred overnight then concentrated. Residue partitioned between EtOAc and water. Aqueous phase extracted with EtOAc and combined organics dried and concentrated. Residue purified by chromatography (silica, 0-100% EtOAc-petrol gradient elution). Title compound obtained as a colourless oil (1.47 g, 87%), 1H NMR (400 MHz, DMSO) 0.00 (3H, s), 0.01 (3H, s), 0.83 (9H, s), 1.76-1.85 (1H, m), 2.23-2.31 (1H, s), 3.71-3.80 (2H, m), 5.66 (1H, dd), 7.57 (1H, t), 7.68 (1H, d), 7.75 (1H, dt), 7.81 (1H, d); MS (ES+) 293.0.

Aufarbeitung

  1. customReaction mixture
  2. concentrationthen concentrated
  3. customResidue partitioned between EtOAc and water
  4. extractionAqueous phase extracted with EtOAc
  5. customcombined organics dried
  6. concentrationconcentrated
  7. customResidue purified by chromatography (silica, 0-100% EtOAc-petrol gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-748b3887af1240b0b088b7c3bbc86a51
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309250B2

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