Trimethylsilyl cyanide → HCID 22734441, compound

HRID 2084772Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:23])[C:7]=1[CH2:8][CH2:9][C:10]1[C:15]2[CH2:16][C:17]([CH3:20])([CH3:19])[O:18][C:14]=2[C:13]([O:21][CH3:22])=[CH:12][CH:11]=1.ClC1[CH:26]=[N:27]C=C(Cl)C=1CC(C1C2CC(C)(C)OC=2C(OC)=CC=1)O.C[Si](C#N)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:26]([CH:9]([C:10]1[C:15]2[CH2:16][C:17]([CH3:20])([CH3:19])[O:18][C:14]=2[C:13]([O:21][CH3:22])=[CH:12][CH:11]=1)[CH2:8][C:7]1[C:6]([Cl:23])=[CH:5][N:4]=[CH:3][C:2]=1[Cl:1])#[N:27]

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-95306a071df143738f9f0a1e8b1080b6
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716987B1

Reaction notes

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