Hydrochloric Acid → HCID 16733444, compound

HRID 1375932Notes

Reaction equation

HRID 1375932 reaction equation
[H-].[Na+].[C:3]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].C([Li])CCC.[CH3:17][CH:18]([CH3:22])[CH2:19][CH:20]=[O:21].Cl>C(OCC)C.O1CCCC1>[CH2:10]([O:9][C:3](=[O:8])[CH2:4][C:5](=[O:6])[CH2:7][CH:20]([OH:21])[CH2:19][CH:18]([CH3:22])[CH3:17])[CH3:11]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8868Ethyl AcetoacetateHCID 115523-MethylbutanalHCID 24758Sodium hydrideHCID 178418339Butyllithium

Product 1

HCID 16733444HCID 16733444, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Sodium hydride, as a 60% mineral oil dispersion, (6.8 g, 169 mmol) was introduced into a dry round bottomed flask, and dry tetrahydrofuran (220 ml) was added thereto. The flask was stoppered with a serum cap, cooled in ice and flushed with nitrogen. Ethyl acetoacetate (20 g, 154 mmol) was added dropwise to the cooled and stirred slurry and the reaction was stirred for 10 minutes after the addition was complete. The solution was cooled at −78° C. and a solution of n-butyl lithium (85 ml of 2M solution in cyclohexane) was added dropwise to the reaction mixture and stirring was continued for a further 10 minutes. 3-Methylbutyraldehyde (154 mmol) was then added in one portion. After a further 10 minutes the reaction was poured in a HCl solution (50 ml of 37% HCl in 400 of water). Diethyl ether was added; the aqueous layer was removed and extracted again with 2×40 ml of diethyl ether. The ethereal extracts were combined, washed with a saturated brine solution, dried over sodium sulfate, filtered, and the solvent removed under reduced pressure. The oily residue was purified by flash chromatography using hexane:ethyl acetate=8:2 as eluent obtaining 16.6 g of 5-hydroxy-7-methyl-3-oxo-octanoic acid ethyl ester. Yield 50%.

Workup

  1. customcap
  2. temperaturecooled in ice
  3. customflushed with nitrogen
  4. temperaturecooled
  5. stirringthe reaction was stirred for 10 minutes
  6. additionafter the addition
  7. stirringstirring
  8. customthe aqueous layer was removed
  9. extractionextracted again with 2×40 ml of diethyl ether
  10. washwashed with a saturated brine solution
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. customthe solvent removed under reduced pressure
  14. customThe oily residue was purified by flash chromatography

Sources & evidence

ORD record
ord-9c8e282f89c340d4b225df27f73217ec
Source dataset
uspto-grants-2007_01
Patent number
US07169890B2

Reaction notes

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