Ethyl Acetate → HCID 12179941, compound

HRID 1987663Notes

Reaction equation

HRID 1987663 reaction equation
C([O:3][C:4]([C@H:6]1[C@H:11]([OH:12])[CH:10]=[CH:9][CH2:8][O:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O>C1COCC1>[OH:3][CH2:4][C@H:6]1[C@H:11]([OH:12])[CH:10]=[CH:9][CH2:8][O:7]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 12179940HCID 12179940, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12179941HCID 12179941, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of trans-3-hydroxy-3,6-dihydro-2H-pyran-2-carboxylic acid ethyl ester (0.480 g, 2.79 mmol) in THF (20 ml) at RT, was added in portions LiAlH4 (0.126 g, 3.384 mmol) and the resulting mixture was stirred for 30 min. EtOAc (10 ml) was added, the mixture was stirred for 10 min and extracted with water (10 ml×2). The organic layer was dried over anhydrous Na2SO4. The solvent was removed in vacuo and the crude product purified by flash chromatography (25-30% EtOAc in hexane).

Workup

  1. stirringthe mixture was stirred for 10 min
  2. extractionextracted with water (10 ml×2)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. customThe solvent was removed in vacuo
  5. customthe crude product purified by flash chromatography (25-30% EtOAc in hexane)

Sources & evidence

ORD record
ord-eb4eedf123dd4accb7ef276a50b052af
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

Loading…