Methanol → (RS)-(2,6-difluoro-4-hydroxy-phenyl)-ethoxy-acetic acid

HRID 1247365Notes

Reaction equation

C([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])C.C1COCC1.CO.O[Li].O>O>[F:15][C:14]1[CH:13]=[C:12]([OH:16])[CH:11]=[C:10]([F:34])[C:9]=1[CH:5]([O:6][CH2:7][CH3:8])[C:4]([OH:35])=[O:3]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (RS)-[4-(tert-butyl-diphenyl-silanyloxy)-2,6-difluoro-phenyl]-ethoxy-acetic acid ethyl ester (10.4 g) in a THF (50 ml), MeOH (50 ml) and H2O (20 ml) mixture was added LiOH.H2O (1.75 g) and it was stirred 2 h at 60° C. After cooling water (240 ml) was added and the solution was washed with TBME (240 ml). The aqueous layer was collected, TBME was added (240 ml) and the mixture was acidified with 1 N HCl sol. The aqueous layer was extracted with one more portion of TBME. The combined organic layers were dried (MgSO4) and the solvent was evaporated to obtained an oil. Solid (RS)-(2,6-difluoro-4-hydroxy-phenyl)-ethoxy-acetic acid (4.6 g, 95%) was obtained after addition of AcOEt, evaporation of it and drying on the high vacuum over night. Off-white solid. MS 231.1 ([M−H]−).

Workup

additionwas added
washthe solution was washed with TBME (240 ml)
customThe aqueous layer was collected
additionTBME was added (240 ml)
extractionwas extracted with one more portion of TBME
dry with materialThe combined organic layers were dried (MgSO4)
customthe solvent was evaporated
customto obtained an oil

Sources & evidence

ORD record: ord-dde7d3eb405547d6bb62e6466d02d228
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129238B2

Reaction notes

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