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

HRID 502056ノート

反応式

HRID 502056 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-1a7883f1d8dd4ef6a1a8e741f10c7fb9
出典データセット
uspto-grants-2010_08
特許番号
US07772425B2

反応ノート

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