Ammonium Chloride → 1-(3-Cyclopropylmethoxy-4-difluoromethoxy-phenyl)-2-(3,5-dichloro-pyridin-4-yl)-ethanol

HRID 241319

Reaction equation

[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=2[O:14][CH:15]([F:17])[F:16])[CH:9]=[O:10])[CH2:3][CH2:2]1.[Cl:18][C:19]1[CH:20]=[N:21][CH:22]=[C:23]([Cl:26])[C:24]=1[CH3:25].CC(C)([O-])C.[K+].[NH4+].[Cl-]>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:9]([OH:10])[CH2:25][C:24]3[C:23]([Cl:26])=[CH:22][N:21]=[CH:20][C:19]=3[Cl:18])[CH:11]=[CH:12][C:13]=2[O:14][CH:15]([F:16])[F:17])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: -30 °C

Procedure

A solution of 3-cyclopropylmethoxy-4-difluoromethoxy-benzaldehyde (5.00 g) and 3,5-dichloro-4-methylpyridine (2.57 g) in 50 ml dry THF was cooled to −30° C. Solid potassium t-butoxide (tBuOK, 1.96 g) was added portionwise maintaining the temperature between −30° C. and −20° C., thus obtaining a dark red solution. After completion of the addition, the mixture was stirred at −30° C. for 1 hour. A saturated aqueous solution of NH4Cl (50 ml) was then added to the reaction mixture, maintaining the temperature between −5° C. and −10° C. The color of the reaction mixture turned to yellow.

Workup

temperaturemaintaining the temperature between −30° C. and −20° C.
customthus obtaining a dark red solution
additionAfter completion of the addition
temperaturemaintaining the temperature between −5° C. and −10° C

Sources & evidence

ORD record: ord-28257fe7af4347e19c75e030fb9f7084
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648204B2

Linked notes

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