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Oxalic Acid → 16-(p-Methylthiophenoxy)hexadeca-5,8,11,14-tetraynoic acid

HRID 1607814
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Reaktionsgleichung

Reaktionsgleichung von HRID 1607814
C([O:3][C:4](=[O:28])[CH2:5][CH2:6][CH2:7][C:8]#[C:9][CH2:10][C:11]#[C:12][CH2:13][C:14]#[C:15][CH2:16][C:17]#[C:18][CH2:19][S:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)C.O1CCCCC1OC1CCCCO1.C(O)(=O)C(O)=O>C(OCC)(=O)C>[CH3:27][C:24]1[CH:25]=[CH:26][C:21]([S:20][CH2:19][C:18]#[C:17][CH2:16][C:15]#[C:14][CH2:13][C:12]#[C:11][CH2:10][C:9]#[C:8][CH2:7][CH2:6][CH2:5][C:4]([OH:28])=[O:3])=[CH:22][CH:23]=1
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Komponenten

5

Edukt 3

HCID 971Oxalic AcidHCID 263182Tetrahydropyranyl etherHCID 7039536816-(p-Methylthiophenoxy)-hexadeca-5,8,11,14-tetraynoic acid ethyl ester

Produkt 1

HCID 1984948016-(p-Methylthiophenoxy)hexadeca-5,8,11,14-tetraynoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1.7 g of 16-(p-methylthiophenoxy)hexadeca-5,8,11,14-tetraynoic acid ethyl ester was mixed with 168 ml of the pH 6.7 buffer solution prepared in accordance with Example 1. The mixture was vigorously stirred and 16.24g of Sigma Lipase, Type VII, from Candida cylindracea were added, stirring was continued for 18 hours at room temperature; the reaction mixture was then transferred to a separatory funnel with 200 ml ethyl acetate and acidified with saturated solution of oxalic acid. The organic layer was separated and the aqueous layer extracted with ethyl acetate. The combinedorganic extract was dried over sodium sulfate and the solvent removed undervacuo. The residue was purified by TLC on silica gel with a Chromatotron using hexane-ethyl acetate (60:40) as the eluant, to yield 16-(p-methylthiophenoxy)hexadeca-5,8,11,14-tetraynoic acid, which was recrystallized from methylene chloride-hexane. M.P. 87°-88° C. (dec).

Aufarbeitung

  1. customprepared in accordance with Example 1
  2. stirringstirring
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. extractionThe combinedorganic extract
  6. dry with materialwas dried over sodium sulfate
  7. customthe solvent removed undervacuo
  8. customThe residue was purified by TLC on silica gel with a Chromatotron

Quellen und Nachweise

ORD-Eintrag
ord-d732c85232e14d02b19dd4a7577cc5bc
Quelldatensatz
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04867915

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