Diisobutylaluminum hydride → Tetrahydro-2H-pyran-3-propanal

HRID 1533883Notes

Reaction equation

HRID 1533883 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][O:9][CH2:8]1)C.CC(C[AlH]CC(C)C)C>>[O:9]1[CH2:10][CH2:11][CH2:12][CH:7]([CH2:6][CH2:5][CH:4]=[O:3])[CH2:8]1

Participants

3

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 15676000Ethyl 3-(tetrahydro-2H-pyran-3-yl)propanoate

Product 1

HCID 15676001Tetrahydro-2H-pyran-3-propanalYield 87.3%

Procedure

To a solution of ethyl-3-(tetrahydro-2H-pyran-3-yl)propionate (3.0 g) was, at -78° C., added dropwise DIBAL (16 ml of 1.5 mole toluene solution) under a nitrogen atmosphere. Stirring was continued for one hour. The reaction was quenched by adding a methanol-water mixture. The resulting solution was allowed to warm up to room temperature. The solids which formed were removed. The filtrate was dried over magnesium sulfate and concentrated to yield a crude oil. The crude product was purified by distillation to yield 2.0 g of the title compound.

Workup

  1. customwas, at -78° C.
  2. customThe reaction was quenched
  3. additionby adding a methanol-water mixture
  4. customThe solids which formed
  5. customwere removed
  6. dry with materialThe filtrate was dried over magnesium sulfate
  7. concentrationconcentrated
  8. customto yield a crude oil
  9. distillationThe crude product was purified by distillation

Sources & evidence

ORD record
ord-366be07a773740a6b7a9ef4746795bc4
Source dataset
uspto-grants-1992_02
Patent number
US05086062

Reaction notes

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