Triethylamine → tert-Butyl 4-hydroxy-2-(hydroxymethyl)-2,3-dihydrobenzofuran-6-carboxylate

HRID 1643669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1643669
[C:1]([O:5][C:6](=[O:33])[C:7]1[CH:12]=[C:11]([O:13]CC2C=CC=CC=2)[C:10]([CH2:21][CH:22]2[CH2:24][O:23]2)=[C:9]([O:25]CC2C=CC=CC=2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.C([O-])([O-])=O.[K+].[K+]>CO.[Pd]>[C:1]([O:5][C:6]([C:7]1[CH:8]=[C:9]([OH:25])[C:10]2[CH2:21][CH:22]([CH2:24][OH:23])[O:13][C:11]=2[CH:12]=1)=[O:33])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 595602363,5-Bis-benzyloxy-4-oxiranylmethyl-benzoic acid tert-butyl ester

Produkt 1

HCID 25067321tert-Butyl 4-hydroxy-2-(hydroxymethyl)-2,3-dihydrobenzofuran-6-carboxylateAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 3,5-bis-benzyloxy-4-oxiranylmethyl-benzoic acid tert-butyl ester (200e) (55 g, 0.12 mol), 10% Pd on Carbon (5 g), Et3N (15 g, 0.14 mol), and K2CO3 (20 g, 0.14 mol) in MeOH (250 mL) was stirred under 760 mmHg of H2 at room temperature for 4 hr. TLC (EtOAc/petroleum oil=1/2) showed the reaction was complete. The mixture was filtered through Celite. The filtrate was concentrated and the residue was purified by column chromatography (EtOAc/petroleum ether=1/3) to give the title compound (18 g, 55% yield) as an off-white solid.

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by column chromatography (EtOAc/petroleum ether=1/3)

Quellen und Nachweise

ORD-Eintrag
ord-1681449ba1764344944a06e5d6a5e666
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119624B2

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