Propylene Glycol → HCID 19068754, compound

HRID 1957261Notes

Reaction equation

[CH2:1]([OH:5])[CH:2]([OH:4])[CH3:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:17][C:18]1[C:19]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([CH:35](OC)OC)[CH:29]=2)=[N:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1>C1(C)C=CC=CC=1>[Cl:17][C:18]1[C:19]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([CH:35]3[O:4][CH:2]([CH3:3])[CH2:1][O:5]3)[CH:29]=2)=[N:20][CH:21]=[C:22]([C:24]([F:26])([F:27])[F:25])[CH:23]=1

Participants

Conditions

Temperature: 23 °C

Procedure

2.0 g of 1,2-propanediol and 100 mg of p-toluenesulfonic acid were added to 3.2 g of 3-chloro-2-(4-chloro-3-dimethoxymethylphenyl)-5-trifluoromethylpyridine in 100 ml of anhydrous toluene. The mixture was then refluxed for two hours and stirred at 23° C. for 16 hours. Extraction was carried out first with 50 ml of a 10% by weight sodium bicarbonate solution and then three times with 80 ml of water each time, after which the organic solution was dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel with cyclohexane/ethyl acetate (10:1). Yield: 3.1 g (94%) of a colorless oil (1:1 mixture of diastereomers);

Workup

temperatureThe mixture was then refluxed for two hours
extractionExtraction
dry with materialthree times with 80 ml of water each time, after which the organic solution was dried over sodium sulfate
concentrationconcentrated
customThe residue was purified by chromatography on silica gel with cyclohexane/ethyl acetate (10:1)

Sources & evidence

ORD record: ord-3e3ee7e2ddfc402e9f9ee2f15c6fb905
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05783522

Reaction notes

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