Potassium Iodide → 4-[4-(methylthio)phenyl]tetrahydro-2H-pyran-4-carbonitrile

HRID 273010Notes

Reaction equation

[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.Br[CH2:13][CH2:14][O:15][CH2:16][CH2:17]Br.[H-].[Na+].[I-].[K+]>>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:10]#[N:11])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:5][CH:4]=1

Participants

Reactant 4

HCID 4875Potassium Iodide

HCID 21521Bis(2-bromoethyl) ether

HCID 24758Sodium hydride

HCID 27600872-(4-(Methylthio)phenyl)acetonitrile

Product 1

HCID 685766134-[4-(methylthio)phenyl]tetrahydro-2H-pyran-4-carbonitrileYield 77%

Procedure

The title compound (5.5 g, 77%, solid after trituration in pentane) was prepared using 4-(methylthio)phenylacetonitrile, bis(2-bromoethyl)ether, sodium hydride and potassium iodide similarly to the procedure used for intermediate 56. Microanalysis: Found: C, 66.62; H, 6.46; N, 5.97%. C13H15NOS requires C, 66.92; H, 6.48; N, 6.00%.

Sources & evidence

ORD record: ord-d5f7c07a194b453e8a04f9ba24e4bd52
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456164B2

Reaction notes

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