Pyridine → HCID 11165106, compound

HRID 1883470Notes

Reaction equation

[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH2:11][OH:12])=[CH:5][CH:4]=1.N1C=CC=CC=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:23]>C(Cl)Cl>[F:14][C:2]([F:13])([F:1])[C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH2:11][O:12][C:22](=[O:23])[O:24][C:25]2[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(4-Trifluoromethyl-phenylsulfanyl)ethanol (15.00 g, 67.50 mmol) prepared in the above Step (1) was dissolved in anhydrous DCM (100 ml), pyridine (7.59 ml, 93.81 mmol) and 4-nitrophenyl chloroformate (13.61 g, 67.50 mmol) were added thereto at 0° C. in order, and the mixture was stirred for 2 hours at room temperature. The reaction was stopped by adding distilled water, and the reaction mixture was extracted with DCM. The organic layer thus extracted was washed with aqueous NH4Cl solution, dried over anhydrous MgSO4, and then concentrated. The concentrate was purified by silica gel column chromatography (DCM/n-hexane=5/1, v/v) to give carbonic acid 4-nitro-phenyl ester 2-(4-trifluoromethyl-phenylsulfanyl)-ethyl ester (22.54 g, 86.21%) of a pale yellow oil.

Workup

additionby adding
distillationdistilled water
extractionthe reaction mixture was extracted with DCM
extractionThe organic layer thus extracted
washwas washed with aqueous NH4Cl solution
dry with materialdried over anhydrous MgSO4
concentrationconcentrated
customThe concentrate was purified by silica gel column chromatography (DCM/n-hexane=5/1

Sources & evidence

ORD record: ord-211d6f6f2a8d45a0967e9783bb329968
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759511B2

Reaction notes

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