Water → 2,2,3,3-Tetramethyl-4,7,10-trioxa-3-silatridec-12-yne

HRID 1792380ノート

反応式

HRID 1792380 の反応式
[Si:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][OH:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].O.[CH3:18][CH2:19][CH2:20]CCC>O1CCCC1.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:20][C:19]#[CH:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 962WaterHCID 8058HexaneHCID 24758Sodium hydrideHCID 111175822-(2-((Tert-butyldimethylsilyl)oxy)ethoxy)ethanol

生成物 1

HCID 235380372,2,3,3-Tetramethyl-4,7,10-trioxa-3-silatridec-12-yne収率 38%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 5-(t-butyldimethylsilyloxy)-3-oxa-1-pentanol (2.16 g, 9.8 mmol) in dry tetrahydrofuran (20 ml) was added sodium hydride (432 mg, 60% in oil, 10.8 mmol) at room temperature. The mixture was stirred for 30 minutes, and propalgyl bromide (2.9 g, 19.6 mmol) was added thereto. The mixture was stirred at room temperature for 12 hours. After the reaction was completed, water was added thereto. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate, and filtered. The organic solvent was removed under reduced pressure to give a crude product. This crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=8:1) to give the title compound (950 mg, yield: 38%).

後処理

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe organic solvent was removed under reduced pressure
  7. customto give a crude product
  8. customThis crude product thus obtained

出典と根拠

ORDレコード
ord-486aeabdab91462684b384f10f955acb
出典データセット
uspto-grants-2006_07
特許番号
US07074819B2

反応ノート

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