4-Toluenesulfonyl chloride → 2,2-Dimethyl-3-(4-pyridyl)-3-(p-tolylsulfonyloxy)propionitrile

HRID 2075891Notes

Reaction equation

C(N(CC)CC)C.[OH:8][CH:9]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[C:10]([CH3:14])([CH3:13])[C:11]#[N:12].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>ClCCl>[CH3:13][C:10]([CH3:14])([CH:9]([C:15]1[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=1)[O:8][S:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)(=[O:29])=[O:28])[C:11]#[N:12]

Participants

Conditions

Temperature: 50 °C

Procedure

Triethylamine (1.57 ml, 11.3 mmol) was added to a solution of 3-hydroxy-2,2-dimethyl-3-(4-pyridyl)propionitrile (1.00 g, 5.67 mmol) in dichloromethane (20 ml) at room temperature. Further, p-toluenesulfonyl chloride (1.30 g, 6.80 mmol) was added to the mixture, and the whole was warmed at 50° C. with stirring for three days. The reaction mixture was allowed to stand and then concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography to give 699 mg (37.4%) of 2,2-dimethyl-3-(4-pyridyl)-3-(p-tolylsulfonyloxy)propionitrile as a pale yellow solid.

Workup

concentrationconcentrated under reduced pressure
customthe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-0e5af12fd4be4fb59d4b9707191ed4cb
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923461B2

Reaction notes

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