Trimethylsilyl cyanide → HCID 22734441, compound

HRID 1057887Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:24])[C:7]=1[CH2:8][CH:9]([C:11]1[C:16]2[CH2:17][C:18]([CH3:21])([CH3:20])[O:19][C:15]=2[C:14]([O:22][CH3:23])=[CH:13][CH:12]=1)O.C[Si]([C:29]#[N:30])(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:29]([CH:9]([C:11]1[C:16]2[CH2:17][C:18]([CH3:21])([CH3:20])[O:19][C:15]=2[C:14]([O:22][CH3:23])=[CH:13][CH:12]=1)[CH2:8][C:7]1[C:2]([Cl:1])=[CH:3][N:4]=[CH:5][C:6]=1[Cl:24])#[N:30]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution (70 ml) obtained in Step A of Example 45 of Compound 45a (2.5 g) in methylene chloride was cooled to 0° C. and then trimethylsilylcyanide (5.4 ml) and boron trifluoride ether complex (2.5 ml) were successively added thereto, followed by stirring at 0° C. for 2 hours. The reaction solution was poured into a saturated aqueous solution of sodium bicarbonate and the mixture was extracted with chloroform. The organic layer was washed with a saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=30/1) to give Compound 63 (0.61 g, 23.8%) as pale-yellow crystals.

Workup

extractionthe mixture was extracted with chloroform
washThe organic layer was washed with a saturated saline
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (chloroform/methanol=30/1)

Sources & evidence

ORD record: ord-0886dcad27e344fb849467969cec173e
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06514996B2

Reaction notes

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