Ethyl formate → HCID 86670263, compound

HRID 1472236Notes

Reaction equation

[CH3:1][C:2]1([CH3:17])[C:7](=[CH2:8])[S:6][C:5](=[N:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[CH2:4][CH2:3]1.C([N-]C(C)C)(C)C.[Li+].[CH:26](OCC)=[O:27].[Cl-].[NH4+]>O1CCCC1>[CH3:1][C:2]1([CH3:17])[C:7](=[CH2:8])[S:6][C:5]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[C:4]([CH:26]=[O:27])[CH2:3]1

Participants

Conditions

Temperature: -78 °C

Procedure

In a dehydrated tetrahydrofuran (15 ml) solution of [5,5-dimethyl-6-methylene-tetrahydro-thiopyran-2-ylidene]-p-tolyl-amine (0.53 g), 2.2 ml of lithium diisopropylamide (1.5 mol/l, tetrahydrofuran/cyclohexane solution) was added dropwise at −78° C. under a nitrogen atmosphere. After stirring at −78° C. for 30 minutes, a tetrahydrofuran (1 ml) solution of ethyl formate (0.24 g) was added dropwise. After raising the temperature to room temperature and further stirring for 1 hour, an aqueous saturated ammonium chloride solution was added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.26 g of the target compound.

Workup

temperatureAfter raising the temperature to room temperature
stirringfurther stirring for 1 hour
extractionthe reaction mixture was extracted with ethyl acetate
washThe organic layer was washed with a saturated saline solution
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-1bd55ad1c0e84af1abf757f952e3c09b
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012493B2

Reaction notes

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