Aluminium lithium hydride → (4-Methyloxan-4-yl)methanol

HRID 1488058Notes

Reaction equation

HRID 1488058 reaction equation
[CH3:1][C:2]1([C:8](OCC)=[O:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][C:2]1([CH2:8][OH:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90021443Ethyl 4-methyltetrahydro-2H-pyran-4-carboxylate2×

Product 1

HCID 59708470(4-Methyloxan-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 100-mL three neck round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of ethyl 4-methyltetrahydro-2H-pyran-4-carboxylate (compound 188.1, 500 mg, 2.90 mmol) in tetrahydrofuran (12 mL). This was followed by the addition of lithium aluminum hydride (221 mg, 5.82 mmol) in portions at 0° C. The reaction mixture was stirred for 1 h at room temperature, then carefully quenched with 1.2 mL of H2O, 1.2 mL of NaOH (15%), 3.5 mL of H2O. The solids were removed by filtration and the filtrate was concentrated under reduced pressure. This resulted in 300 mg (crude) of the title compound as a yellow oil.

Workup

  1. customInto a 100-mL three neck round-bottom flask, which was purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customcarefully quenched with 1.2 mL of H2O, 1.2 mL of NaOH (15%), 3.5 mL of H2O
  4. customThe solids were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4911033d391f4d1e9c8ab68b289c6569
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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