Dimethyl Sulfide → HCID 23316758, compound

HRID 1982486Notes

Reaction equation

[CH3:1][C:2]1([CH3:14])[CH2:6][O:5][CH:4]([C:7]2[S:8][CH:9]=[CH:10][C:11]=2[O:12][CH3:13])[NH:3]1.C([Li])CCC.[CH3:20][S:21]C>O1CCCC1.CCCCCC>[CH3:1][C:2]1([CH3:14])[CH2:6][O:5][CH:4]([C:7]2[S:8][C:9]([S:21][CH3:20])=[CH:10][C:11]=2[O:12][CH3:13])[NH:3]1

Participants

Conditions

Temperature: -45 °C

Procedure

27 g (0.128 moles) of 3,4-dihydro-4,4-dimethyl-2-(3-methoxy-2-thienyl)-oxazole are dissolved in 400 ml of absolute tetrahydrofuran, the solution is cooled to -45° C. and 88 ml (0.141 moles) of a 1.6 molar solution of butyllithium in n-hexane is added dropwise such that the temperature in the reaction mixture does not exceed -45° C. After completion of the addition it is stirred further for 1.5 hours at -45° C., a solution of 13.9 g (0.147 moles) of dimethylsulfide in 70 ml of absolute tetrahydrofuran is added and stirring continues for an additional 30 minutes at this temperature. Then it is heated to -20° C., poured onto water and extracted several times with ether. The combined ether phases are dried with sodium sulfate, decolored with activated charcoal, evaporated in vacuo and the crystalline residue is recrystallized from petroleum ether. Yield: 24.7 g (75%), m.p. 56°-58° C.

Workup

customdoes not exceed -45° C
additionAfter completion of the addition it
stirringstirring
waitcontinues for an additional 30 minutes at this temperature
temperatureThen it is heated to -20° C.
additionpoured onto water
extractionextracted several times with ether
dry with materialThe combined ether phases are dried with sodium sulfate
customevaporated in vacuo
customthe crystalline residue is recrystallized from petroleum ether

Sources & evidence

ORD record: ord-4606adc650354468a39bcafaf2b5ce91
Source dataset: uspto-grants-1986_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04596830

Reaction notes

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