Tetrahydrofuran → (4-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-benzyloxy)-acetic acid

HRID 230820노트

반응식

HRID 230820 반응식
C[O:2][C:3](=[O:41])[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]([O:31][Si](C(C)(C)C)(C)C)[C:27]([CH3:30])([CH3:29])[CH3:28])=[C:20]([CH3:39])[CH:19]=2)([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][C:8]=1[CH3:40].C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[OH-].[Na+]>O>[CH2:14]([C:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:6][O:5][CH2:4][C:3]([OH:41])=[O:2])=[C:8]([CH3:40])[CH:9]=1)([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]([OH:31])[C:27]([CH3:29])([CH3:30])[CH3:28])=[C:20]([CH3:39])[CH:19]=1)[CH2:16][CH3:17])[CH3:15]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 2724141Tetrabutylammonium FluorideHCID 57763463[4-(1-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-benzyloxy]-acetic acid methyl ester

생성물 1

HCID 57763426(4-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-benzyloxy)-acetic acid수율 60.4%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of enantiomer 1 of [4-(1-{4-[2-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-benzyloxy]-acetic acid methyl ester (0.96 g, 1.64 mmol) and THF (10 mL) is added 1M TBAF (3.3 mL, 3.28 mmol). The solution is heated at a reflux overnight and concentrated. The residue is dissolved in MeOH (5 mL) and water (1 mL), NaOH (0.33 g, 8.21 mmol) is added and the solution is heated at reflux for 3 hours. The solution is concentration, dissolved in EtOAc (20 mL), washed with 1M HCl (15 mL), water (15 mL), brine (15 mL), dried over MgSO4, and concentrated. The residue is chromatographed to furnish the title compound (0.45 g, 0.99 mmol, 60%).

후처리

  1. temperatureThe solution is heated at a reflux overnight
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in MeOH (5 mL)
  4. temperaturethe solution is heated
  5. temperatureat reflux for 3 hours
  6. concentrationconcentration
  7. dissolutiondissolved in EtOAc (20 mL)
  8. washwashed with 1M HCl (15 mL), water (15 mL), brine (15 mL)
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated
  11. customThe residue is chromatographed

출처 및 근거

ORD 기록
ord-fb226fd1141240c083418946d8e04b64
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566803B2

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