Aluminium lithium hydride → HCID 12179942, compound

HRID 1987664Notes

Reaction equation

HRID 1987664 reaction equation
C([O:3][C:4]([C@H:6]1[C@@H:11]([O:12]C(=O)C)[CH:10]=[CH:9][CH2:8][O:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:3][CH2:4][C@H:6]1[C@@H:11]([OH:12])[CH:10]=[CH:9][CH2:8][O:7]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57723929HCID 57723929, compound

Product 1

HCID 12179942HCID 12179942, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of cis-3-acetoxy-3,6-dihydro-2H-pyran-2-carboxylic acid ethyl ester (52 mg, 0.25 mmol) in THF (5 ml) was added LiAlH4 (60 mg, 1.60 mmol). The resulting solution was stirred at ambient temperature for 15 min. The reaction was quenched by addition of H2O (10 ml). The solution was diluted with EtOAc (50 ml×2), washed with brine (50 ml), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography with 20% EtOAc-hexane to give cis-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol

Workup

  1. customThe reaction was quenched by addition of H2O (10 ml)
  2. additionThe solution was diluted with EtOAc (50 ml×2)
  3. washwashed with brine (50 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography with 20% EtOAc-hexane

Sources & evidence

ORD record
ord-421a4575d96b4b1497545a3a57b45d4d
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

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