Water → HCID 59563735, compound

HRID 1944182Notes

Reaction equation

HRID 1944182 reaction equation
[C:1]1([CH:7]([CH2:12][O:13][Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])[C:8]([O:10]C)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-].O>C1COCC1.O.CO>[C:1]1([CH:7]([CH2:12][O:13][Si:14]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:21]([CH3:22])[CH3:23])[C:8]([OH:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 59563766HCID 59563766, compound

Product 1

HCID 59563735HCID 59563735, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To methyl 2-phenyl-3-(triisopropylsilyloxy)propanoate (E399) in THF/H2O/MeOH was added LiOH*H2O and the solution was stir at room temperature overnight. The solution was poured into NH4Cl(sat)/HCl (1 N) (3:1) and extracted with EtOAc. The combined organics were dried (Na2SO4), filtered, and evaporated. Column chromatography (0%-4% MeOH/CH2Cl2) gave pure 2-phenyl-3-(triisopropylsilyloxy)propanoic acid (E400).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-f958568f495e416285c20d2b51dabd79
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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