반응 #65818

반응 방정식

Sodium hydride

methyl(R)-3-hydroxytetradecanoate

2-bromooctanoyl chloride

→

tetradecanoic acid methyl ester

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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.

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