Water → HCID 22399035, compound

HRID 1734141Notes

Reaction equation

HRID 1734141 reaction equation
[O:1]=[C:2]([CH3:15])[CH2:3][CH:4]([C:10](OCC)=[O:11])[C:5](OCC)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[OH:6][CH2:5][CH:4]([CH2:3][CH:2]([OH:1])[CH3:15])[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 962WaterHCID 12000252Diethyl (2-oxopropyl)propanedioateHCID 21226445Aluminium lithium hydride

Product 1

HCID 22399035HCID 22399035, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 11.4 g of diethyl 2-oxopropylmalonate in 30 ml of tetrahydrofuran was added dropwise under ice-cooling over 20 minutes to a suspension of 5.00 g of lithium aluminum hydride in 100 ml of tetrahydrofuran. The reaction fluid was stirred for an hour under ice-cooling and for 4.5 hours at room temperature, and 10 ml of water was added thereto dropwise under ice-cooling over 20 minutes. The reaction fluid was refluxed for an hour and filtrated. The unfiltered solid was suspended in 200 ml of ethanol and the suspension was refluxed. The suspension was filtrated, and the filtrate combined with the foregoing filtrate was concentrated under a reduced pressure to obtain 7.08 g of 2-hydroxymethyl-1,4-pentanediol as a colorless oily matter.

Workup

  1. temperaturedropwise under ice-cooling over 20 minutes
  2. temperatureThe reaction fluid was refluxed for an hour
  3. filtrationfiltrated
  4. temperaturethe suspension was refluxed
  5. filtrationThe suspension was filtrated
  6. concentrationwas concentrated under a reduced pressure

Sources & evidence

ORD record
ord-23dbd7f8a4a843dda0537faf08c1fcb4
Source dataset
uspto-grants-1996_07
Patent number
US05532365

Reaction notes

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