Sodium hydride → Triisopropyl[(3-methylthien-2-yl)methoxy]silane

HRID 9672

Reaction equation

HRID 9672 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][OH:8].[H-].[Na+].[H][H].[CH:13]([Si:16](Cl)([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])([CH3:15])[CH3:14]>O1CCCC1.C(OCC)(=O)C>[CH:13]([Si:16]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[O:8][CH2:7][C:3]1[S:4][CH:5]=[CH:6][C:2]=1[CH3:1])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 12875263(3-Methylthiophen-2-yl)methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 21986297Triisopropyl[(3-methylthien-2-yl)methoxy]silane

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3-methylthien-2-yl)methanol (3.20 g) in tetrahydrofuran (10 ml) was added to a mixture of sodium hydride (60% dispersion in mineral oil, 1.05 g) in tetrahydrofuran (40 ml). After the evolution of hydrogen had subsided triisopropylsilyl chloride (5.2 ml) was added. The reaction mixture was stirred for 2 hours then diluted with ethyl acetate. The mixture was extracted with water, 2M aqueous sodium hydroxide, water and dried with brine and over sodium sulfate. The crude product was purified by Biotage chromatography® using 100:1 petroleum ether:ethyl acetate as eluent to give the title compound as a colorless oil.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with water, 2M aqueous sodium hydroxide, water
  3. dry with materialdried with brine and over sodium sulfate
  4. customThe crude product was purified by Biotage chromatography®

Sources & evidence

ORD record
ord-bb369774dd52483faa7fe8c2c2fb6a6b
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Linked notes

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