Ethyl Acetate → HCID 57427615, compound

HRID 1804776Notes

Reaction equation

HRID 1804776 reaction equation
C[C:2]1(C)[CH2:12][C:11](=O)[C:5]2[C:6]([CH2:9][OH:10])=[CH:7][O:8][C:4]=2[CH2:3]1.[Li]CCCC.CCOC(C)=O>C1COCC1>[O:8]1[C:4]2[CH:3]=[CH:2][CH:12]=[CH:11][C:5]=2[C@H:6]([CH2:9][OH:10])[CH2:7]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 59152683HCID 59152683, compoundHCID 178418339Butyllithium

Product 1

HCID 57427615HCID 57427615, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The crude oxirane 19 from above (2.4 g, 7.84 mmol) is dissolved in 50 ml of THF and cooled to −78° C. in a dry-ice bath. At this temperature, n-BuLi (1.6M in hexane, 4.9 ml, 7.84 mmol) is added drop wise. The mixture is then stirred for one hour and allowed to warm up to 0° C. After careful hydrolysis and extraction with EtOAc the crude is purified by Flash-chromatography (ethyl acetate/hexanes (from 5:95 to 25:75), silicagel).

Workup

  1. temperatureto warm up to 0° C
  2. customis purified by Flash-chromatography (ethyl acetate/hexanes (from 5:95 to 25:75), silicagel)

Sources & evidence

ORD record
ord-de730abaa0784f0799220e408a8aebee
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

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