HCID 10013476, compound → HCID 10441722, compound

HRID 1987662Notes

Reaction equation

HRID 1987662 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][CH:6]1[CH:11]([OH:12])[CH:10]=[CH:9][CH2:8][O:7]1

Participants

4

Reactant 2

HCID 10013476HCID 10013476, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10441722HCID 10441722, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-3-acetoxy-3,6-dihydro-2H-pyran-2-carboxylic acid ethyl ester (56 mg, 0.26 mmol) in THF (5 ml) was added LiAlH4 (62 mg, 1.64 mmol). The resulting solution was stirred at ambient temperature for 15 min and 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 (Rf=0.25 in EtOAc) to give 2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol as a colorless liquid

Workup

  1. customquenched 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 (Rf=0.25 in EtOAc)

Sources & evidence

ORD record
ord-3116008ae9764045a88a62c8487d03d7
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

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