Imidazole → Methyl 4-(1-{4-[2-(t-butyldimethylsilanyloxy)-3,3-dimethyl-butoxy]-3-methylphenyl}-1-ethylpropyl)-2-methyl-benzoate

HRID 230809ノート

反応式

HRID 230809 の反応式
[OH:1][CH:2]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH3:26])[CH:17]=2)([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:7][C:6]=1[CH3:27].N1C=CN=C1.[CH3:37][C:38]([Si:41](Cl)([CH3:43])[CH3:42])([CH3:40])[CH3:39]>CN(C=O)C>[Si:41]([O:1][CH:2]([C:28]([CH3:29])([CH3:31])[CH3:30])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH3:26])[CH:17]=2)([CH2:12][CH3:13])[CH2:14][CH3:15])=[CH:7][C:6]=1[CH3:27])([C:38]([CH3:40])([CH3:39])[CH3:37])([CH3:43])[CH3:42]

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 10320279Methyl 4-(1-{4-[2-(hydroxy)-3,3-dimethyl-butoxy]-3-methylphenyl}-1-ethylpropyl)-2-methylbenzoate

生成物 1

HCID 57763479Methyl 4-(1-{4-[2-(t-butyldimethylsilanyloxy)-3,3-dimethyl-butoxy]-3-methylphenyl}-1-ethylpropyl)-2-methyl-benzoate収率 72%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of the methyl 4-(1-{4-[2-(hydroxy)-3,3-dimethyl-butoxy]-3-methylphenyl}-1-ethylpropyl)-2-methylbenzoate (4.79 g, 11.24 mmol), Example 1, in DMF (40 mL) is added imidazole (1.14 g, 16.87 mmol) followed by the addition of TBSCl (1.78 g, 11.80 mmol). The mixture is stirred at RT overnight and concentrated. The mixture is partitioned between 0.1 M HCl (100 mL) and EtOAc (100 mL). The aqueous layer is extracted with EtOAC. The combined organic layers is MgSO4 dried, concentrated, and chromatographed (10% EtOAc/Hex) to give the title compound (4.37 g, 72%).

後処理

  1. concentrationconcentrated
  2. customThe mixture is partitioned between 0.1 M HCl (100 mL) and EtOAc (100 mL)
  3. extractionThe aqueous layer is extracted with EtOAC
  4. customdried
  5. concentrationconcentrated
  6. customchromatographed (10% EtOAc/Hex)

出典と根拠

ORDレコード
ord-ddca908e5a80451b8305d891dd7e9100
出典データセット
uspto-grants-2009_07
特許番号
US07566803B2

反応ノート

読み込み中…