Propanoic acid, 2-bromo-2-methyl-, ethyl ester → 6-Methoxy-2-naphthaldehyde

HRID 372941

Reaktionsgleichung

Reaktionsgleichung von HRID 372941
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13](OCC)=[O:14])[CH:7]=[CH:6]2.COC1C=C2C(=CC=1)C=C(C#N)C=C2.BrC(C)(C)C(OCC)=O.[BH4-].[Na+]>C(O)C.[Zn]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]=[O:14])[CH:7]=[CH:6]2

Komponenten

7

Edukt 4

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 226777Ethyl 6-methoxy-2-naphthoateHCID 3491736-Methoxynaphthalene-2-carbonitrileHCID 4311764Sodium borohydride

Produkt 1

HCID 769916-Methoxy-2-naphthaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

6-methoxy-2-naphthaldehyde (substrate IIA) was synthesized from 6-methoxy-2-carbethoxynaphthalene, prepared from 6-methoxy-2-naphthonitrile, ethyl 2-bromoisobutyrate, and zinc dust as described by Horeau et al., 1947, Bull. Soc. Chim. Fr. 14:53-59. The keto-ester intermediate, mp 74°-76° C. (lit. 72.5-73.5° C.) was reduced to the corresponding secondary alcohol ester with sodium borohydride in ethanol at 4° C. and then thermally decomposed (Horeau et al. 1953, Compt. Rend. 236:826-8) to afford the final compound. The aldehyde was 25 purified either by zone sublimation or via the bisulfite adduct; mp 80°-81.5° C.; (lit. 79° C. Horeau et al., 1953, supra: lit. 81°-82° C. Gandhi et al., 1955 J. Chem. Soc., 2530).

Quellen und Nachweise

ORD-Eintrag
ord-cb80d53f8a0441b0bf973772abcbb211
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05162203

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