Propyl mercaptan → HCID 20216939, compound

HRID 236273Notes

Reaction equation

C([Li])CCC.C(S)CC.[CH2:10]=[CH:11][CH2:12][S:13](=O)(=O)[S:14]/[CH:15]=[CH:16]/[CH2:17][S:18](=[O:23])(=[O:22])[CH2:19][CH:20]=[CH2:21]>O1CCCC1>[CH3:10][CH2:11][CH2:12][S:13][S:14]/[CH:15]=[CH:16]/[CH2:17][S:18](=[O:23])(=[O:22])[CH2:19][CH:20]=[CH2:21]

Participants

Conditions

Temperature: 0 °C

Procedure

n-Butyllithium (75.5 μL, 0.106 m. mole) was added to a solution of 1-propane thiol (8.66 mg, 0.114 m. mole) in dry tetrahydrofuran (1.5 ml) under Argon with stirring at 0° C. This solution was added dropwise to a solution of (E)-4,5,9-trithiadodeca-1,6,11-triene 4,4,9,9-tetraoxide (30 mg, 1.106 m. mole) in tetrahydrofuran (5 ml) at -20° C. with stirring under Argon. The reaction mixture was stirred at -20° C. for 15 minutes, allowed to warm to room temperature and quenched by the addition of a saturated solution of ammonium chloride (3.0 ml) and methylene chloride (15 ml). The organic layer is separated, washed with water (5 ml), dried (magnesium sulfate) and concentrated under vacuum to give 26 mg of (E)-4,5,9-trithiadodeca-6,11-diene 9,9-dioxide product (97% yield) characterized by IR, Proton and Carbon 13 NMR spectroscopy.

Workup

stirringwith stirring under Argon
stirringThe reaction mixture was stirred at -20° C. for 15 minutes
temperatureto warm to room temperature
customquenched by the addition of a saturated solution of ammonium chloride (3.0 ml) and methylene chloride (15 ml)
customThe organic layer is separated
washwashed with water (5 ml)
dry with materialdried (magnesium sulfate)
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-ada3595dc7b54aa3ab22531a575c1077
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04643994

Reaction notes

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