2-Allyl-2-ethylmalonic acid diethyl ester → HCID 21324160, compound

HRID 1927659Notes

Reaction equation

HRID 1927659 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[C:11]([CH2:19][CH:20]=[CH2:21])([CH2:17][CH3:18])[C:12](OCC)=[O:13])C>C1COCC1>[CH2:19]([C:11]([CH2:17][CH3:18])([CH2:12][OH:13])[CH2:10][OH:9])[CH:20]=[CH2:21]

Participants

4

Reactant 2

HCID 2972362-Allyl-2-ethylmalonic acid diethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 21324160HCID 21324160, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of lithium aluminum hydride (7.8 g, 0.20 mol) in THF (350 mL) was added 2-allyl-2-ethylmalonic acid diethyl ester (23.5 g, 0.10 mol) in THF (150 mL) over 2 h. After stirring at rt for 2 days, the reaction was carefully quenched with dilute sulfuric acid (7%, 250 mL). The product was extracted with diethyl ether (3×100 mL) and ethyl acetate (3×100 mL), and the combined extracts were washed with brine (300 mL), dried over sodium sulfate and concentrated to give 2-allyl-2-ethylpropane-1,3-diol.

Workup

  1. customthe reaction was carefully quenched with dilute sulfuric acid (7%, 250 mL)
  2. extractionThe product was extracted with diethyl ether (3×100 mL) and ethyl acetate (3×100 mL)
  3. washthe combined extracts were washed with brine (300 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a3c9451868a9461c88271610e696b6f9
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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