Citric Acid → (r)-3-Triisopropylsilyloxybutyric acid

HRID 1954254Notes

Reaction equation

HRID 1954254 reaction equation
[CH:1]([Si:4]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[O:5][C@H:6]([CH3:13])[CH2:7][C:8]([O:10]CC)=[O:9])([CH3:3])[CH3:2].[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.O>[CH:17]([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:14]([CH3:16])[CH3:15])[O:5][C@H:6]([CH3:13])[CH2:7][C:8]([OH:10])=[O:9])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 54538409Ethyl (r)-(-)-3-triisopropylsilyloxybutyrate

Product 1

HCID 14084664(r)-3-Triisopropylsilyloxybutyric acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

0.0755 mol (21.78 g) of the product from stage 1 is stirred at 60° C. for 5 days in 1.51 liters of a 0.01 molar lithium hydroxide solution in a tetrahydrofuran/water 1:1 mixture. The mixture is acidified with aqueous citric acid and the product is extracted with ethyl acetate. The organic phase is washed with water, dried over sodium sulfate and concentrated under reduced pressure.

Workup

  1. extractionthe product is extracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cfd387cc3af548c889a76d959ca0cd13
Source dataset
uspto-grants-2000_09
Patent number
US06121316

Reaction notes

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