Sodium hydride → 2-(4-(2-Methoxyethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 57521

反応式

HRID 57521 の反応式
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[O:3]1.[H-].[Na+].[CH3:19][O:20][CH2:21][CH2:22]Br>CN(C=O)C>[CH3:19][O:20][CH2:21][CH2:22][O:15][C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

生成物 1

HCID 684654432-(4-(2-Methoxyethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane収率 60.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (150 mg, 0.682 mmol) in DMF (5 mL) was added 60% NaH (136 mg, 3.41 mmol) and 2-bromoethyl methyl ether (0.13 mL, 1.363 mmol). The resulting solution was stirred at 50° C. overnight, cooled to ambient temperature, quenched with water, and extracted with EtOAc. The combined extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography to give the title compound (114 mg, 60% yield).

後処理

  1. temperaturecooled to ambient temperature
  2. customquenched with water
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-54b3315cffc04387a3fc58752d298f1b
出典データセット
uspto-grants-2016_09
特許番号
US09434726B2

関連ノート

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