Sodium hydride → Methyl Myristate

HRID 37540

Reaktionsgleichung

Reaktionsgleichung von HRID 37540
[H-].[Na+].O[C@H:4]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:5][C:6]([O:8][CH3:9])=[O:7].BrC(CCCCCC)C(Cl)=O>O1CCCC1>[CH3:9][O:8][C:6](=[O:7])[CH2:5][CH2:4][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 98349453R-hydroxymyristic acid methyl esterHCID 110756072-bromooctanoyl Chloride

Produkt 1

HCID 31284Methyl Myristate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

98 mg (3.3 mmol) Sodium hydride (80% in mineral oil) was added to a solution of 764 mg (2.96 mmol) methyl(R)-3-hydroxytetradecanoate in 20.0 mL tetrahydrofuran. After 25 minutes, a solution of 732 mg (3.03 mmol) 2-bromooctanoyl chloride in 10.0 mL tetrahydrofuran was added dropwise via syringe to the cloudy off-white mixture. After 10 minutes at 0° C., the reaction flask was removed from the cold bath for 24 hours. The mixture was poured into 100 mL 10% NaHCO3 and extraction with ether (3×50 mL) was performed. Drying over MgSO4 and removal of the solvent by rotary evaporation gave yellow oil. Purification by flash chromatography (3×24 cm column, 50% CH2Cl2 /hexane) gave 407 mg (30% yield based on methyl (R)-3-hydroxytetradecanoate) (R)-3-[2-bromo-1-oxooctyl)oxy]tetradecanoic acid methyl ester.

Aufarbeitung

  1. waitAfter 10 minutes at 0° C.
  2. customthe reaction flask was removed from the cold bath for 24 hours
  3. additionThe mixture was poured into 100 mL 10% NaHCO3 and extraction with ether (3×50 mL)
  4. dry with materialDrying over MgSO4 and removal of the solvent by rotary evaporation
  5. customgave yellow oil
  6. customPurification by flash chromatography (3×24 cm column, 50% CH2Cl2 /hexane)

Quellen und Nachweise

ORD-Eintrag
ord-402c59967d624e84bde9292ad1b5115b
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420305

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