Ammonium Chloride → 4-Ethinyl-1,5-dimethyl-3-(trifluoromethyl)-1h-pyrazole

HRID 895687Notes

Reaction equation

Cl[CH:2]=[CH:3][C:4]1[C:5]([C:11]([F:14])([F:13])[F:12])=[N:6][N:7]([CH3:10])[C:8]=1[CH3:9].CC(C)([O-])C.[K+].[NH4+].[Cl-]>C1COCC1>[C:3]([C:4]1[C:5]([C:11]([F:13])([F:14])[F:12])=[N:6][N:7]([CH3:10])[C:8]=1[CH3:9])#[CH:2]

Participants

Conditions

Temperature: 0 °C

Procedure

1.27 g (5.67 mmol) of 4-(2-chloroethenyl)-1,5-dimethyl-3-(trifluoromethyl)-1H-pyrazole are dissolved in 40 ml of dry THF and placed under a protective gas atmosphere. After the reaction solution has been cooled to 0° C., 1.91 g (17.0 mmol) of potassium tert-butoxide are introduced and, on completion of addition, the mixture is stirred at 20° C. for 3 h. After the end of the reaction, a saturated NH4Cl solution (25 ml) is added and extraction is effected twice with CH2C12. The combined organic phases are dried over MgSO4 and concentrated. The product is obtained as a solid in a 79% yield.

Workup

customAfter the end of the reaction
extractionextraction
dry with materialThe combined organic phases are dried over MgSO4
concentrationconcentrated
customThe product is obtained as a solid in a 79% yield

Sources & evidence

ORD record: ord-34160cca40854d22b9e2d86126e203eb
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916839B2

Reaction notes

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