1-Hexanol → Dihexyl ether

HRID 359758

Reaktionsgleichung

Reaktionsgleichung von HRID 359758
CCC1C2N=C(C=C3C(C=C)=C(C)C(=CC4[C@@H:32]([CH3:33])[C@H:31]([CH2:34][CH2:35][C:36]([OH:38])=O)C(=C(CC(O)=O)C5NC(C=2)=C(C)C=5C(O)=O)N=4)N3)C=1C.Br.C(O)(=O)C.[CH2:50](O)[CH2:51][CH2:52][CH2:53][CH2:54][CH3:55].CCC1C(C)=C2NC=1C=C1N=C3C(C(C(C(OC)=O)C3=C3N=C(C=C4NC(=C2)C(C=C)=C4C)C(C)C3CCC(OC)=O)=O)=C1C>>[CH2:50]([O:38][CH2:36][CH2:35][CH2:34][CH2:31][CH2:32][CH3:33])[CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]

Komponenten

5

Edukt 4

HCID 81031-HexanolHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 138978174(2S-trans)-18-Carboxy-20-(carboxymethyl)-13-ethyl-2,3-dihydro-3,7,12,17-tetramethyl-8-vinyl-21H,23H-porphine-2-propionic acid; (17S,18S)-18-(2-Carboxyethyl)-20-(carboxymethyl)-12-ethenyl-7-ethyl-3,8,13,17-tetramethyl-17,18,22,23-tetrahydroporphyrin-2-carboxylic acidHCID 178435490HCID 178435490, Verbindung

Produkt 1

HCID 8198Dihexyl etherAusbeute 68 %

Versuchsvorschrift

The chlorin-e6 tetramethyl ester prepared in Example 2 (50 mg) was reacted with HBr/acetic acid and n-hexyl alcohol as described in Example 1 for methyl pheophorbide. The desired product was isolated in 68% yield, and the purity confirmed by TLC and HPLC. The structure was confirmed by NMR and mass spectroscopy; the spectra also showed evidence for aggregation of two chlorin units.

Quellen und Nachweise

ORD-Eintrag
ord-c5e0e9607d044cb39ffdf4aee866d473
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US05002962

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