Diethyl 2-(2-(benzyloxy)ethyl)malonate → 2-[2-(Benzyloxy)ethyl]propane-1,3-diol

HRID 1368676Notes

Reaction equation

HRID 1368676 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][CH2:15][CH2:16][CH:17]([C:23](OCC)=[O:24])[C:18](OCC)=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CCOCC>[CH2:7]([O:14][CH2:15][CH2:16][CH:17]([CH2:18][OH:19])[CH2:23][OH:24])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 12549951Diethyl 2-(2-(benzyloxy)ethyl)malonateHCID 21226445Aluminium lithium hydride

Product 1

HCID 105126392-[2-(Benzyloxy)ethyl]propane-1,3-diolYield 87.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a cooled, stirred suspension of lithium aluminium hydride (103 g, 2.7 mol) in dry ether (2.51) under nitrogen was added ethyl 4-benzyloxy-2-ethoxycarbonyl-butanoate (362 g, 1.23 mol) over a period of 3 hours. On completion of the addition, the reaction mixture was allowed to warm to room temperature, and then heated under reflux for 1 hour. It was then re-cooled and the excess lithium aluminium hydride destroyed by dropwise addition of water (100 ml), 2M sodium hydroxide (100 ml) and water (300 ml). The reaction mixture was filtered, and the filter cake washed well with chloroform. The filtrate was dried (MgSO4), filtered, and evaporated to give 4-benzyloxy-2-hydroxymethylbutan-1-ol as a clear oil (226 g, 87%). δH (CDCl3) 1.35-2.05 (3H, m, CHCH2CH2), 3.30-3.80 (8H, m, 3×CH2O, 2×OH), 4.42 (2H, s, OCH2Ph), 7.26 (5H, s, Ar).

Workup

  1. additionOn completion of the addition
  2. temperatureheated
  3. temperatureunder reflux for 1 hour
  4. temperatureIt was then re-cooled
  5. customthe excess lithium aluminium hydride destroyed by dropwise addition of water (100 ml), 2M sodium hydroxide (100 ml) and water (300 ml)
  6. filtrationThe reaction mixture was filtered
  7. washthe filter cake washed well with chloroform
  8. dry with materialThe filtrate was dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-3b37295a7736438e91b1a8bdf12514f5
Source dataset
uspto-grants-2003_06
Patent number
US06573378B1

Reaction notes

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