Carbon Dioxide → Propiolic Acid

HRID 265626

Reaktionsgleichung

Reaktionsgleichung von HRID 265626
[C-]#[C-].[Li+:3].[Li+].C[O:6]CCl.BrC[C:11]1[C:12]([O:16]C)=NO[CH:15]=1.[C:18]1(C(C2C=CC=CC=2)OC2C(CI)=NSN=2)C=CC=C[CH:19]=1.C(=O)=O>O1CCCC1>[C:12]([OH:16])(=[O:6])[C:11]#[CH:15].[C-:18]#[C-:19].[Li+:3].[Li+:3]

Komponenten

8

Edukt 5

HCID 280Carbon Dioxide2×HCID 7864Chloromethyl Methyl EtherHCID 19034573HCID 19034573, VerbindungHCID 22906284HCID 22906284, VerbindungHCID 178462446HCID 178462446, Verbindung2×

Produkt 2

HCID 10110Propiolic AcidHCID 178462446HCID 178462446, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Dibromoolefin intermediate XIX is then converted to ethynyl intermediate XX. Treatment of the dibromoolefin intermediate with about two equivalents of n-butyllithium produces the lithium acetylide XX, wherein R13 is Li. This transformation is typically carried out in a polar organic solvent, such as tetrahydrofuran, at a temperature of about -78° C. to about 25° C. The lithium acetylide is reacted with electrophiles, such as methoxymethyl chloride, bromomethyl-3-methoxyisoxazole, 3-diphenylmethoxy-4-iodomethyl-1,2,5-thiadiazole, carbon dioxide, tetrazole disulfide, and the like, to prepare the formula I compounds. In a typical example, the lithium acetylide is treated with solid CO2 at a temperature of about -78° C. to about -60° C. to produce propargylic acid intermediate XX wherein R13 is CO2H. This compound may be further modified as described herein.

Aufarbeitung

  1. customthe like, to prepare the formula I compounds

Quellen und Nachweise

ORD-Eintrag
ord-ce298877670641c59331bb92e48a1590
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648492

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