Sodium hydride → Methyl 2-(3-((t-butyldimethylsilyl)oxy)phenoxy)acetate

HRID 1051104ノート

反応式

HRID 1051104 の反応式
[H-].[Na+].[Si:3]([O:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21]>CN(C)C=O>[Si:3]([O:10][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[O:17][CH2:19][C:20]([O:22][CH3:23])=[O:21])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 114474403-[(Tert-butyldimethylsilyl)oxy]phenol

生成物 1

HCID 125464147Methyl 2-(3-((t-butyldimethylsilyl)oxy)phenoxy)acetate収率 77%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

Sodium hydride (60% mineral oil dispersion, 0.35 g, 8.7 mmol) was added to a solution of 3-((t-butyldimethylsilyl)oxy)phenol (0.49 g, 2.2 mmol), methyl 2-bromoacetate (0.37 g, 2.4 mmol), and dimethylformamide (2 mL) in a 50 mL round bottom flask under a nitrogen atmosphere at room temperature. The solution was heated in a 50° C. oil bath and allowed to stir overnight for approximately 16 hours. The resulting mixture was cooled to room temperature. The reaction was quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (200 mL). The organic extract was dried (Na2SO4), filtered and concentrated. The resulting crude residue was purified by combiflash (40 g column, hexanes→100% ethyl acetate/hexanes, gradient) to afford 0.5 g (77%) of methyl 2-(3-((t-butyldimethylsilyl)oxy)phenoxy)acetate.

後処理

  1. temperatureThe resulting mixture was cooled to room temperature
  2. customThe reaction was quenched with saturated aqueous ammonium chloride (100 mL)
  3. extractionextracted with ethyl acetate (200 mL)
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting crude residue was purified by combiflash (40 g column, hexanes→100% ethyl acetate/hexanes, gradient)

出典と根拠

ORDレコード
ord-88e1e745a34e4e5fb8215360fe003fe8
出典データセット
uspto-grants-2016_07
特許番号
US09388153B2

反応ノート

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