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

HRID 502056노트

반응식

HRID 502056 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-1a7883f1d8dd4ef6a1a8e741f10c7fb9
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772425B2

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