Water → (RS)-(2,6-difluoro-4-hydroxy-phenyl)-ethoxy-acetic acid ethyl ester

HRID 1247367Notes

Reaction equation

HRID 1247367 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[CH:5]([C:9]1[C:14]([F:15])=[CH:13][C:12]([O:16][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:11][C:10]=1[F:34])[O:6][CH2:7][CH3:8])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[CH2:1]([O:3][C:4](=[O:35])[CH:5]([C:9]1[C:14]([F:15])=[CH:13][C:12]([OH:16])=[CH:11][C:10]=1[F:34])[O:6][CH2:7][CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 69292045(RS)-[4-(tert-butyl-diphenyl-silanyloxy)-2,6-difluoro-phenyl]-ethoxy-acetic acid ethyl ester

Product 1

HCID 69290842(RS)-(2,6-difluoro-4-hydroxy-phenyl)-ethoxy-acetic acid ethyl esterYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(RS)-[4-(tert-Butyl-diphenyl-silanyloxy)-2,6-difluoro-phenyl]-ethoxy-acetic acid ethyl ester (6.85 g) was dissolved in THF (135 ml) and a 1 M TBAF sol. in THF (15.1 ml) was added. After 3 h the reaction mixture was poured on AcOEt (300 ml) and H2O (300 ml). The aqueous layer was extracted with two more portions of AcOEt (100 ml). The combined organic layers were washed with brine and dried (MgSO4) and the solvent was evaporated. Crystallization from ice cold CH2Cl2 afforded 3.08 g (86%) of (RS)-(2,6-difluoro-4-hydroxy-phenyl)-ethoxy-acetic acid ethyl ester. White crystals. MS 258.9 ([M−H]+).

Workup

  1. extractionThe aqueous layer was extracted with two more portions of AcOEt (100 ml)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated
  5. customCrystallization from ice cold CH2Cl2

Sources & evidence

ORD record
ord-828e8014ec5542d9a9e6ce307a3e5619
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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