Hydrochloric Acid → 3-Cyclopropyl-1-[4-(methylsulphenyl)-phenyl]-propan-1,3-dione

HRID 21453

Reaction equation

[CH3:1][C:2]([CH:4]1[CH2:6][CH2:5]1)=[O:3].[H-].[Na+].[CH3:9][S:10][C:11]1[CH:21]=[CH:20][C:14]([C:15](OCC)=[O:16])=[CH:13][CH:12]=1.Cl>O1CCOCC1>[CH:4]1([C:2](=[O:3])[CH2:1][C:15]([C:14]2[CH:20]=[CH:21][C:11]([S:10][CH3:9])=[CH:12][CH:13]=2)=[O:16])[CH2:6][CH2:5]1

Participants

Conditions

Temperature: 60 °C

Procedure

Cyclopropyl methyl ketone (0.84 g) was added to a suspension of sodium hydride (80%, 0.3 g) in dioxane. The mixture was stirred for 20 minutes and ethyl 4-(methylsulphenyl)benzoate (1.0 g) was added. The mixture was stirred and heated at 45° C. for 1.5 hours and at 60° C. for 2 hours. It was left to stand at room temperature overnight. Hydrochloric acid (2M) was added and the mixture was extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The flitrate was evaporated to dryness and the residue was purified by chromatography eluted with a mixture of ethyl acetate and hexane to give 3-cyclopropyl-1-[4-(methylsulphenyl)-phenyl]-propan-1,3-dione (0.59 g) as an orange solid, NMR (CDCl3) 1.0(m,2H), 1.2(m,2H), 1.8(m, 1H), 2.5(s,3H), 6.25(s,1H), 7.25(d,2H), 7.8(d,2H), 16.35(bs,1H).

Workup

stirringThe mixture was stirred
waitIt was left
waitto stand at room temperature overnight
extractionthe mixture was extracted with ethyl acetate
washwashed with water
dry with materialdried (MgSO4)
filtrationfiltered
customThe flitrate was evaporated to dryness
customthe residue was purified by chromatography
washeluted with a mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-ff81f5e3b81e4e9384c51fa1f0552849
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05424276

Linked notes

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