Aluminium lithium hydride → (5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methanol

HRID 1770801Notes

Reaction equation

HRID 1770801 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[CH2:14][O:13][CH2:12][CH2:11][C:10]=2[C:15](OCC)=[O:16])=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:1]([N:4]1[C:8]([C:9]2[CH2:14][O:13][CH2:12][CH2:11][C:10]=2[CH2:15][OH:16])=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90409040ethyl 5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-carboxylate

Product 1

HCID 90408368(5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methanolYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of ethyl 5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-carboxylate (600 mg, 2.27 mmol) in THF (10 mL) was added LiAlH4 (1M in THF, 2.72 mL, 2.72 mmol) at −20° C., the reaction was stirred at −20° C. for 30 min, and was quenched with Sat. NH4Cl, the aqueous layer was extracted with EtOAc, the combined organics were washed with brine, dried and concentrated to give crude oil, which was purified by column (Hexanes/EtOAc=100:0 to 20:80) to give (5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methanol (500 mg).

Workup

  1. customwas quenched with Sat. NH4Cl
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washthe combined organics were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give crude oil, which
  7. customwas purified by column (Hexanes/EtOAc=100:0 to 20:80)

Sources & evidence

ORD record
ord-0898f9270df4423da89a956595bb8a96
Source dataset
uspto-grants-2016_02
Patent number
US09248199B2

Reaction notes

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