Tetrabutylammonium Fluoride → HCID 12822858, compound

HRID 2259225Notes

Reaction equation

HRID 2259225 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 1M 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-a6e5ae61a68f41e8ba73f48359b9af20
Source dataset
uspto-grants-1995_12
Patent number
US05472959

Reaction notes

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