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

HRID 1484789
Notes
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Reaction equation

HRID 1484789 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-6e93903ca60a4712b4638eb8683b0066
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09422279B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes