Bis(dimethylaminoethyl) ether → 1-(3,4-Dichlorophenyl)-1-propanone

HRID 2279484Notes

Reaction equation

O(CCN(C)C)CCN(C)C.[CH2:12]([Mg]Br)[CH3:13].[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[Cl:26])[C:20](Cl)=[O:21]>C1COCC1>[Cl:16][C:17]1[CH:18]=[C:19]([C:20](=[O:21])[CH2:12][CH3:13])[CH:23]=[CH:24][C:25]=1[Cl:26]

Participants

Conditions

Temperature: -60 °C

Procedure

To a solution of THF (100 mL) and 2,2′-oxybis(N,N-dimethylethanamine) (9.18 g, 57.3 mmol) cooled to 0° C. was added ethylmagnesium bromide (19.1 mL, 57.3 mmol, 3N in THF) and stirred for 10 min. The solution was cooled to −60° C. and a solution of 3,4-dichlorobenzoyl chloride (10.0 g, 47.7 mmol) in THF (20 mL) was added dropwise over 10 min. The reaction was stirred for 1 h, quenched by adding sat'd. NH4Cl sat. and extracted with EtOAc. The combined extracts were dried with (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography (Biotage 40M) eluting an EtOAc/hexane gradient (2 to 10% EtOAc) to afford 6.0 g (85%, 53% pure) 1-(3,4-dichlorophenyl)propan-1-one (156) as clear oil which was used without additional purification.

Workup

stirringThe reaction was stirred for 1 h
customquenched
additionby adding sat'd
extractionNH4Cl sat. and extracted with EtOAc
dry with materialThe combined extracts were dried with (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified by SiO2 chromatography (Biotage 40M)
washeluting an EtOAc/hexane gradient (2 to 10% EtOAc)

Sources & evidence

ORD record: ord-7b63c9b4b2824b0ba013c7d7fca4726a
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133187B2

Reaction notes

Loading…