Imidazole → 2-[(tert-Butyldimethylsilyl)oxymethyl]-6-methoxybenzyl alcohol

HRID 1766908ノート

反応式

HRID 1766908 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][OH:10])[C:4]=1[CH2:11][OH:12].N1C=CN=C1.[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19].O>O1CCCC1>[Si:22]([O:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[CH2:11][OH:12])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:24])[CH3:23]

参加物

6

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 14892485(3-Methoxy-1,2-phenylene)dimethanol

生成物 1

HCID 468330582-[(tert-Butyldimethylsilyl)oxymethyl]-6-methoxybenzyl alcohol収率 53%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

3-Methoxy-1,2-benzenedimethanol (1.30 g, 7.73 mmol) obtained from Example 21-(1) was dissolved in tetrahydrofuran (15 ml), and imidazole (526.2 mg, 7.73 mmol) and tert-butylchlorodimethylsilane (1.165 g, 7.73 mmol) were added thereto at 0° C. with stirring. The mixture was stirred at room temperature for 2 hours, then water was added thereto, and the product was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and the solvent was distilled off under reduced pressure. The residue was subjected to chromatography on a silica gel (60 g) column (eluent; ethyl acetate:hexane=1:4) to afford the title compound (1.156 g, 53% yield) as an oil.

後処理

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-253902a73572476d84f71ec61421d186
出典データセット
uspto-grants-2007_06
特許番号
US07230023B2

反応ノート

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