Hydrochloric Acid → HCID 66874614, Verbindung

HRID 1799634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1799634
[H-].[Na+].[Br-].[C:4]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:6])=[O:5].[F:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=1.Cl>O1CCCC1.O>[F:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:4]([OH:6])=[O:5])=[CH:37][CH:36]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 10918084Phosphonium, (8-carboxyoctyl)triphenyl-, bromide

Produkt 1

HCID 66874614HCID 66874614, VerbindungAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydride (60% dispersion in mineral oil; 0.65 g, 16 mmol) was added portionwise at room temperature to a stirred solution of (8-carboxy-octyl)-triphenyl-phosphonium bromide (2.8 g, 5.6 mmol) in tetrahydrofuran (30 mL) at room temperature, then after 1 hour 4-fluorobenzaldehyde (700 mg, 5.64 mmol) was added portionwise to the reaction mixture and the solution stirred for 2 days at room temperature. On reaction completion, water (10 ml) was added and the solution acidified to pH 3 with concentrated hydrochloric acid. The product was extracted with ethyl acetate, the organic layer dried over magnesium sulfate, filtered and evaporated. Chromatography (SiO2, heptane-ethyl acetate 4:1) afforded 10-(4-fluoro-phenyl)-dec-9-enoic acid (280 mg, 19%) as a colorless oil.

Aufarbeitung

  1. additionwas added
  2. extractionThe product was extracted with ethyl acetate
  3. dry with materialthe organic layer dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3b555ebeff164425a7d18e0383631ef6
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344027B2

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