Tetrabutylammonium Fluoride → HCID 12822858, compound

HRID 375796Notes

Reaction equation

HRID 375796 reaction equation
[C:1]1([CH2:7][C:8]([CH2:20][C:21]([OH:23])=[O:22])([CH3:19])[C:9]([O:11][Si](C(C)(C)C)(C)C)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]1([CH2:7][C:8]([CH2:20][C:21]([OH:23])=[O:22])([CH3:19])[C:9]([OH:11])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86749013HCID 86749013, compound

Product 1

HCID 12822858HCID 12822858, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 3-phenyl-2-methylcarboxymethylpropionic acid, t-butyldimethylsilyl ester (3.07 g, 9.13 mmol) in tetrahydrofuran (11 mL) and place under an argon atmosphere. Add, by dropwise addition, tetra-n-butylammonium fluoride (11 mL of a 1 M solution in tetrahydrofuran, 11 mmol). Stir for 1 hour at room temperature and partition between ethyl ether and water. Separate the organic phase, wash with saturated aqueous sodium chloride, dry (MgSO4), filter and evaporate the solvent in vacuo to give 3-phenyl-2-methylcarboxymethylpropionic acid.

Workup

  1. custompartition between ethyl ether and water
  2. customSeparate the organic phase
  3. washwash with saturated aqueous sodium chloride
  4. dry with materialdry (MgSO4)
  5. filtrationfilter
  6. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-129dfac5f61c4400b67fbd150277d09d
Source dataset
uspto-grants-1996_01
Patent number
US05488047

Reaction notes

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