Allyl bromide → [Rac]-3-(3-allyl-4-hydroxy-naphthalen-1-yl)-2-ethoxy-propionic acid ethyl ester

HRID 479246

Reaktionsgleichung

[CH2:1]([O:3][C:4](=[O:24])[CH:5]([O:21][CH2:22][CH3:23])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17]CC=C)=[CH:9][CH:8]=1)[CH3:2].C(O[C:28](=O)[CH:29](OCC)[CH2:30]C1C2C(=CC=CC=2)C(O)=CC=1)C.C(Br)C=C.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:24])[CH:5]([O:21][CH2:22][CH3:23])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[C:9]([CH2:30][CH:29]=[CH2:28])[CH:8]=1)[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

0.87 g (2.65 mmol) [rac]-3-(4-allyloxy-naphthalen-1-yl)-2-ethoxy-propionic acid ethyl ester [prepared from [rac]-2-ethoxy-3-(4-hydroxy-naphthalen-1-yl)-propionic acid ethyl ester (example 150 a] and allylbromide, potassium carbonate in acetone at 60° C.] was stirred for 2 hours at 160° C. without any solvent. The dark residue was purified by flash chromatography (silica gel, hexane/AcOEt=4:1) to yield 0.82 g (94%) of [rac]-3-(3-allyl-4-hydroxy-naphthalen-1-yl)-2-ethoxy-propionic acid ethyl ester as yellow oil.

Aufarbeitung

customThe dark residue was purified by flash chromatography (silica gel, hexane/AcOEt=4:1)

Quellen und Nachweise

ORD-Eintrag: ord-5fdaa05bc7494ac5a2f0226384b2d8b5
Quelldatensatz: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06642389B2

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