HCID 19918581, compound → 2-Benzyl-3-hydroxypropanoic acid

HRID 1755830Notes

Reaction equation

HRID 1755830 reaction equation
[CH2:1]([CH:8]([C:19]([O-])=[O:20])[C:9]([O:11]CC1C=CC=CC=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:20][CH2:19][CH:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 19918581HCID 19918581, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 5623452-Benzyl-3-hydroxypropanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

benzyl 2-benzyl malonate (75) is treated with lithium aluminum hydride in THF at -78° C. The reaction is allowed to warm to room temperature and then is quenched with aqueous HCl. The reaction mixture is diluted with water and extracted with ethyl acetate. After drying over Na2SO4, the ethyl acetate is evaporated and the product purified by flash chromatography over silica gel to give (76).

Workup

  1. customis quenched with aqueous HCl
  2. additionThe reaction mixture is diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialAfter drying over Na2SO4
  5. customthe ethyl acetate is evaporated
  6. customthe product purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-078050ee019d45ed9ce207d90070bd04
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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