Diethyl Ether → 2-(Oxan-4-yl)ethan-1-ol

HRID 1350120Notes

Reaction equation

HRID 1350120 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[CH2:12][CH2:11][CH:10]([CH2:13][C:14](OCC)=[O:15])[CH2:9][CH2:8]1.CCOCC.[OH-].[Na+]>C1COCC1>[O:7]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][OH:15])[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 2773412Ethyl tetrahydropyran-4-ylacetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 177509442-(Oxan-4-yl)ethan-1-olYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring suspension of lithium aluminum hydride (5.10 g, 138 mmol) in THF (200 mL) at 0° C. was added drop-wise a solution of ethyl 2-(4-oxanyl)acetate (22.0 g, 138 mmol) in THF (50 mL). The reaction mixture was then heated at reflux overnight. After cooling the mixture in an ice bath, ether (300 mL) was added, followed by drop-wise addition of 5N NaOH, until the formation of heavy white precipitate is complete. The suspension was filtered and the filtrate dried (K2CO3), filtered and concentrated by rotary evaporation to give a colorless liquid (17.7 g, 100%).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling the mixture in an ice bath
  4. filtrationThe suspension was filtered
  5. dry with materialthe filtrate dried (K2CO3)
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-b59c375e005549f7b2b5bb4c760dbc4d
Source dataset
uspto-grants-2007_05
Patent number
US07214686B2

Reaction notes

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