Chlorotrimethylsilane → [Methoxy(tetrahydro-4H-pyran-4-ylidene)methoxy](trimethyl)silane

HRID 2410319Notes

Reaction equation

HRID 2410319 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[O:13]1[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15][CH2:14]1.[CH3:23][Si:24](Cl)([CH3:26])[CH3:25]>O1CCCC1>[CH3:22][O:21][C:19](=[C:16]1[CH2:17][CH2:18][O:13][CH2:14][CH2:15]1)[O:20][Si:24]([CH3:26])([CH3:25])[CH3:23]

Participants

6

Reactant 4

HCID 6397Chlorotrimethylsilane2×HCID 7912DiisopropylamineHCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl esterHCID 178418339Butyllithium

Product 1

HCID 24897138[Methoxy(tetrahydro-4H-pyran-4-ylidene)methoxy](trimethyl)silane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of diisopropylamine (5.2 mL, 37 mmol) in tetrahydrofuran (15 mL) was added dropwise n-butyllithium (1.6 M in hexane, 21 mL, 34 mmol) at 0° C. and stirred for 20 min. A mixture of methyl tetrahydro-2H-pyran-4-carboxylate (4.5 g, 31 mmol) and trimethylsilyl chloride (4.3 mL, 34 mmol) was added to the mixture at −40° C., then trimethylsilyl chloride (0.4 mL, 0.3 mmol) was added to the mixture. The mixture was stirred at room temperature for 2 h. The volatile components were removed by evaporation and the residual mixture was filtered through a pad of celite washing with hexane. The filtrate was evaporated to give 6.9 g (quant.) of the title compound as a clear yellow oil.

Workup

  1. additionwas added to the mixture at −40° C.
  2. stirringThe mixture was stirred at room temperature for 2 h
  3. customThe volatile components were removed by evaporation
  4. filtrationthe residual mixture was filtered through a pad of celite
  5. washwashing with hexane
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-3c5ce0d5047f43478467428c9529784a
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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