Sodium Thiosulfate → HCID 117759796, compound

HRID 1049575Notes

Reaction equation

ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][O:13][CH2:14][O:15][CH2:16][C:17]1[CH:18]=[C:19](/[CH:23]=[CH:24]/[CH2:25][CH2:26][C:27]#[N:28])[CH:20]=[CH:21][CH:22]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)(=O)C>[CH3:12][O:13][CH2:14][O:15][CH2:16][C:17]1[CH:18]=[C:19]([CH:23]2[O:9][CH:24]2[CH2:25][CH2:26][C:27]#[N:28])[CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

m-Chloroperbenzoic acid (3.77 g) was added to a solution of (E)-5-(3-((methoxymethoxy)methyl)phenyl)pent-4-enenitrile (2.08 g) in ethyl acetate (20 mL) at room temperature, and the mixture was stirred at 80° C. for 1 hr. Saturated aqueous sodium thiosulfate solution was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (1.07 g) as a colorless oil.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record: ord-5405172d30dc42e2b3c14dbfbcca4803
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

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