Water → HCID 10419436, compound

HRID 1987671Notes

Reaction equation

HRID 1987671 reaction equation
C([O:3][C:4](=O)[C:5]([O:10][CH2:11][CH:12]=[CH2:13])=[C:6]([OH:9])[CH2:7][CH3:8])C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1.CCOC(C)=O>[CH2:11]([O:10][CH:5]([CH:6]([OH:9])[CH:7]=[CH2:8])[CH2:4][OH:3])[CH:12]=[CH2:13]

Participants

6

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 86606933HCID 86606933, compound

Product 1

HCID 10419436HCID 10419436, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-allyloxy-3-hydroxy-pentenoic acid ethyl ester (200 mg, 1.00 mmol) in THF (5 mL) was added LiAlH4 (151 mg, 4.00 mmol). The resulting solution was stirred at ambient temperature for 15 min. H2O (10 mL) was added and the mixture was diluted with EtOAc (50 mL×2), washed with brine (50 mL), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography with 50% EtOAc-hexane

Workup

  1. washwashed with brine (50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography with 50% EtOAc-hexane

Sources & evidence

ORD record
ord-e0798c9f573b4d15a1ab8f86bd28f5d5
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

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