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

HRID 1247381ノート

反応式

HRID 1247381 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

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]−).

後処理

  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

出典と根拠

ORDレコード
ord-b5fe155d56594b88ba2bffe8f3974b7d
出典データセット
uspto-grants-2006_10
特許番号
US07129238B2

反応ノート

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