Ethyl oxoacetate → Ethyl 3-cyclopropyl-2-hydroxy-propanoate

HRID 56660

Reaction equation

HRID 56660 reaction equation
[O:1]=[CH:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].Br[Mg][CH2:10][CH:11]1[CH2:13][CH2:12]1>C1COCC1.C(OCC)(=O)C>[CH:11]1([CH2:10][CH:2]([OH:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 70211Ethyl oxoacetateHCID 178419657HCID 178419657, compound

Product 1

HCID 116489250Ethyl 3-cyclopropyl-2-hydroxy-propanoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under argon and with ice cooling, a solution of 5.4 g (purity 50%, 26.7 mmol) of ethyl oxoacetate in 50 ml of THF was quickly added dropwise to 7.6 g (48 mmol, 1.8 eq.) of bromo(cyclopropylmethyl)magnesium. The reaction mixture was stirred for another 48 h, diluted with ethyl acetate and quenched with water. Celite was added, and the reaction mixture was stirred for 5 min and then filtered. After phase separation, the organic phase was washed once with water, dried (sodium sulphate), filtered and concentrated under reduced pressure. Yield: 2.6 g (60% of theory)

Workup

  1. customquenched with water
  2. additionCelite was added
  3. stirringthe reaction mixture was stirred for 5 min
  4. filtrationfiltered
  5. customAfter phase separation
  6. washthe organic phase was washed once with water
  7. dry with materialdried (sodium sulphate)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27e22d2fb738441eb0d64cce107c8a92
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Linked notes

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