Imidazole → Methyl {[tert-butyl(dimethyl)silyl]oxy}(4-methoxyphenyl)acetate

HRID 1171771ノート

反応式

HRID 1171771 の反応式
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].N1C=CN=C1.[OH:14][CH:15]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[C:16]([O:18][CH3:19])=[O:17].O>CN(C=O)C>[Si:5]([O:14][CH:15]([C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)[C:16]([O:18][CH3:19])=[O:17])([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6]

参加物

6

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 523496Methyl 2-hydroxy-2-(4-methoxyphenyl)acetate

生成物 1

HCID 86623126Methyl {[tert-butyl(dimethyl)silyl]oxy}(4-methoxyphenyl)acetate収率 97.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

TBDMSCl (1.5 g, 9.94 mmol) and imidazole (1.0 g, 14.6 mmol) were added to a solution of methyl hydroxy-(4-methoxyphenyl)acetate (Teodozyj Kolasa et al., J. Org. Chem., 1987, 22, 4978-4984) (1.3 g, 6.62 mmol) in DMF (8 mL) and the mixture was stirred at r.t. for 2 h. Water was added and the mixture was extracted with diethyl ether. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated to give the title compound (2.0 g, 97%).

後処理

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-8c065bb14b334bd5901077221dadb90f
出典データセット
uspto-grants-2010_11
特許番号
US07829707B2

反応ノート

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