Water → (RS)-(2,6-difluoro-3-hydroxy-phenyl)-ethoxy-acetic acid

HRID 1247381

반응식

HRID 1247381 반응식
C([O:3][C:4](=[O:35])[CH:5]([C:9]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]([O:16][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[C:10]=1[F:34])[O:6][CH2:7][CH3:8])C.O.O[Li].O>C1COCC1.CO>[F:34][C:10]1[C:11]([OH:16])=[CH:12][CH:13]=[C:14]([F:15])[C:9]=1[CH:5]([O:6][CH2:7][CH3:8])[C:4]([OH:35])=[O:3]

참가 물질

6

반응물 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 69290209(RS)-[3-(tert-butyl-diphenyl-silanyloxy)-2,6-difluoro-phenyl]-ethoxy-acetic acid ethyl ester

생성물 1

HCID 21905416(RS)-(2,6-difluoro-3-hydroxy-phenyl)-ethoxy-acetic acid수율 99%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
65 °C

실험 절차

To a solution of (RS)-[3-(tert-butyl-diphenyl-silanyloxy)-2,6-difluoro-phenyl]-ethoxy-acetic acid ethyl ester (62.5 g) in THF (250 ml) and MeOH (250 ml) was added H2O (200 ml) and LiOH.H2O (10.5 g) and it was stirred 2 h at 65° C. MeOH and THF were evaporated and the aqueous residue was washed with Hept/Et2O 9:1 (2×150 ml). The organic layers were extracted with two portions of H2O (200 ml). The combined aqueous layers were cooled in an ice bath and acidified with 35 ml 25% aq. HCl. Extraction with AcOEt (3×200 ml) followed by washing with brine, drying (Na2SO4) and evaporation of the solvent afforded 28.7 g (99%) of (RS)-(2,6-difluoro-3-hydroxy-phenyl)-ethoxy-acetic acid. Yellow viscous oil. MS 231.2 ([M−H]−).

후처리

  1. customMeOH and THF were evaporated
  2. washthe aqueous residue was washed with Hept/Et2O 9:1 (2×150 ml)
  3. extractionThe organic layers were extracted with two portions of H2O (200 ml)
  4. temperatureThe combined aqueous layers were cooled in an ice bath
  5. extractionExtraction with AcOEt (3×200 ml)
  6. washby washing with brine
  7. customdrying
  8. custom(Na2SO4) and evaporation of the solvent

출처 및 근거

ORD 기록
ord-b5fe155d56594b88ba2bffe8f3974b7d
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129238B2

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