Hydrochloric Acid → (3-Methylthiophen-2-yl)(4-propylphenyl)methanone

HRID 1469201Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5](OCC)=[CH:4][CH:3]=1.[Li][CH2:12][CH2:13][CH2:14]C.CON(C)[C:19]([C:21]1[S:22][CH:23]=[CH:24][C:25]=1[CH3:26])=[O:20].Cl>C1COCC1>[CH3:26][C:25]1[CH:24]=[CH:23][S:22][C:21]=1[C:19]([C:2]1[CH:3]=[CH:4][C:5]([CH2:12][CH2:13][CH3:14])=[CH:6][CH:7]=1)=[O:20]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 4-bromophenetole (1.86 mL, 13.0 mmol) in anhydrous THF (15 mL) was added dropwise (over a 5-min period) a solution of n-BuLi (6.0 mL, 2.5 M in hexane) under nitrogen atmosphere at −78° C. The resulting mixture was stirred at −78° C. for 1 hour, and then a solution of the Weinreb amide 43 (1.85 g, 10.0 mmol) in anhydrous THF (5.0 mL) was added dropwise (over a 10-min period). The reaction mixture was allowed to warm to room temperature and stirred for 16 hours. The mixture was poured into a 1 M HCl solution (25 mL) and extracted with EtOAc (50 mL). The organic phase was subsequently washed with brine, dried over MgSO4 and evaporated under vacuum. The residue was further purified by silica column chromatography (Biotage) to provide (4-ethoxyphenyl)(3-methylthiophen-2-yl)methanone (44, 1.52 g, 6.16 mmol, 62%).

Workup

temperatureto warm to room temperature
stirringstirred for 16 hours
extractionextracted with EtOAc (50 mL)
washThe organic phase was subsequently washed with brine
dry with materialdried over MgSO4
customevaporated under vacuum
customThe residue was further purified by silica column chromatography (Biotage)

Sources & evidence

ORD record: ord-3ba859f9ba104090af2929a15cbc8a55
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006187B2

Reaction notes

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