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

HRID 1484795
Notes
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Reaction equation

HRID 1484795 reaction equation
[C:1]1([C:7]2[CH2:12][O:11][CH2:10][CH2:9][C:8]=2[C:13](OCC)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]1([C:7]2[CH2:12][O:11][CH2:10][CH2:9][C:8]=2[CH2:13][OH:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67311476ethyl 5-phenyl-3,6-dihydro-2H-pyran-4-carboxylate

Product 1

HCID 90417308(5-phenyl-3,6-dihydro-2H-pyran-4-yl)methanolYield 83.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of ethyl 5-phenyl-3,6-dihydro-2H-pyran-4-carboxylate (1.05 g, 4.52 mmol) in THF (20 mL) was added LiAlH4 (1M in THF, 5.42 mL, 5.42 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 35:65) to give (5-phenyl-3,6-dihydro-2H-pyran-4-yl)methanol (720 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 35:65)

Sources & evidence

ORD record
ord-fe017942113f4bc1a8e55fde8b49eecc
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