Diethyl Ether → HCID 57497168, compound

Temperature

-15 °C

A solution of 4-chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid methoxy-methyl-amide (930 mg, 3.9 mmol) in tetrahydrofuran (30 ml) was cooled to 0° C. and treated dropwise with a solution of lithium aluminium hydride in tetrahydrofuran (1M, 2 ml). Stirring was continued at 0° C. for 45 minutes. In order to complete the reaction, another 2 ml of the solution of lithium aluminium hydride in tetrahydrofuran (1M) was added. After 45 minutes the reaction mixtures was cooled to −15° C. and a saturated solution of potassium hydrogensulphate (25 ml) was added dropwise. Stirring was continued at −15° C. for 10 minutes, then ether (30 ml) was added and again stirred for 30 minutes. Thereafter, the reaction mixture was left to warm to room temperature, the organic layer separated, washed with water, finally dried over sodium sulphate and evaporated. The crude material was purified by chromatography on silica gel using a 4:1-mixture of cyclohexane and ethyl acetate as the eluent. The 4-chloro-1-difluoromethyl-1H-pyrazole-3-carbaldehyde was obtained as a colourless oil (582 mg, 83%).

1. customthe reaction
2. customAfter 45 minutes the reaction mixtures
3. stirringStirring
4. waitwas continued at −15° C. for 10 minutes
5. stirringagain stirred for 30 minutes
6. waitThereafter, the reaction mixture was left
7. temperatureto warm to room temperature
8. customthe organic layer separated
9. washwashed with water
10. dry with materialfinally dried over sodium sulphate
11. customevaporated
12. customThe crude material was purified by chromatography on silica gel using a 4

ORD record

ord-eb708e43fdee4472b93599a211d392cb

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242943B2