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

HRID 230820ノート

反応式

HRID 230820 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-fb226fd1141240c083418946d8e04b64
出典データセット
uspto-grants-2009_07
特許番号
US07566803B2

反応ノート

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