Water → 3-(Furan-3-yl)propan-1-ol

HRID 611215Notes

Reaction equation

HRID 611215 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14](OCC)=[O:15])=[CH:8]1.C(OCC)(=O)C.O>CCOCC>[O:7]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][OH:15])=[CH:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 92549Ethyl furan-3-propionateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 135212383-(Furan-3-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of 1.05 g (27.6 mmol) of lithium aluminum hydride in 100 ml of ether, a solution of 3.090 g (18.37 mmol) of ethyl 3-(3-furyl)propionate in 20 ml of ether was added dropwise under ice-cooling, followed by stirring at room temperature for 1 hour. To decompose the excess lithium aluminum hydride, ethyl acetate was added dropwise to the reaction mixture under ice-cooling; subsequently, water was added until a white precipitate formed. The white precipitate was filtered using Celite and washed with ethyl acetate 3 times. The combined filtrate was evaporated under reduced pressure. The obtained crude 3-(3-furyl)propanol was used for the next reaction without purification.

Workup

  1. temperaturecooling
  2. additionwas added dropwise to the reaction mixture under ice-
  3. temperaturecooling
  4. customformed
  5. filtrationThe white precipitate was filtered
  6. washwashed with ethyl acetate 3 times
  7. customThe combined filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d62c80cd54de431aa143b7597c242643
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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