Water → Benzoic Acid

HRID 1020118Notes

Reaction equation

HRID 1020118 reaction equation
[Si](OCC1SC(C(CN2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)C2=O)C(OC)=O)=CC=1)(C(C)(C)C)(C)C.[Li+].[OH-:33].O>C1COCC1.O>[C:29]([OH:30])(=[O:33])[C:28]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 59563713Methyl 2-(5-((tert-butyldimethylsilyloxy)methyl)thiophen-2-yl)-3-(1,3-dioxoisoindolin-2-yl)propanoate

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 1

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

Procedure

To methyl 2-(5-((tert-butyldimethylsilyloxy)methyl)thiophen-2-yl)-3-(1,3-dioxoisoindolin-2-yl)propanoate (E233) in THF/H2O was added LiOH*H2O, and the solution was stirred for 1.5 h or until complete conversion to product was visible by LC-MS. The solution was then poured into EtOAc/NH4Cl(sat)/1 N HCl (3:1) and the aqueous layer was further extracted with EtOAc. The organics were dried (Na2SO4), filtered, evaporated, and dried to give crude 2-(2-(5-(tert-butyldimethylsilyloxy)methyl)thiophen-2-yl)-2-carboxyethylcarbamoyl)benzoic acid (E234).

Workup

  1. extractionthe aqueous layer was further extracted with EtOAc
  2. dry with materialThe organics were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customdried

Sources & evidence

ORD record
ord-f1dd5c63a23740cba27c025862022337
Source dataset
uspto-grants-2014_05
Patent number
US08716310B2

Reaction notes

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