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

HRID 1247367노트

반응식

HRID 1247367 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

(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]+).

후처리

  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

출처 및 근거

ORD 기록
ord-828e8014ec5542d9a9e6ce307a3e5619
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129238B2

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