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

HRID 2380200Notes

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 filtrate 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 filtrate was evaporated to dryness
customthe residue was purified by chromatography
washeluted with a mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-5e87dcc7f5e6417eb3942d1c7df2dc63
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05366957

Reaction notes

Loading…