Trimethylsilyl cyanide → HCID 15480789, compound

HRID 842948Notes

Reaction equation

HRID 842948 reaction equation
[CH2:1]1[O:23][C:4]2([CH2:9][CH2:8][C:7](O)([C:10]3[C:19]4[O:18][CH2:17][CH2:16][O:15][C:14]=4[C:13]([O:20][CH3:21])=[CH:12][CH:11]=3)[CH2:6][CH2:5]2)[O:3][CH2:2]1.C[Si]([C:28]#[N:29])(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]1[O:23][C:4]2([CH2:9][CH2:8][C:7]([C:28]#[N:29])([C:10]3[C:19]4[O:18][CH2:17][CH2:16][O:15][C:14]=4[C:13]([O:20][CH3:21])=[CH:12][CH:11]=3)[CH2:6][CH2:5]2)[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 12052213HCID 12052213, compound

Product 1

HCID 15480789HCID 15480789, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Compound 2a (0.49 g, 1.5 mmol) obtained in Step A in dichloromethane (4.9 mL), trimethylsilyl cyanide (0.26 mL, 1.9 mmol) was added at −78° C., then boron trifluoride-ethyl ether complex (0.20 mL, 1.6 mmol) was added dropwise, and the mixture was stirred for 10 minutes, followed by stirring at room temperature for 10 minutes. A saturated aqueous solution of sodium bicarbonate was added and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried over sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate=2/1) to give Compound 2 (0.30 g, 61%)as a colorless oil.

Workup

  1. additionboron trifluoride-ethyl ether complex (0.20 mL, 1.6 mmol) was added dropwise
  2. stirringby stirring at room temperature for 10 minutes
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-df3b7500dbd845369e946c43f9575d7f
Source dataset
uspto-grants-2002_04
Patent number
US06376535B2

Reaction notes

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