2-Thiophenecarboxaldehyde → 2-(3,5-Dimethyl-phenyl)-1-thien-2-yl-ethylamine
Reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.C[Si](C)(C)[NH:10][Si](C)(C)C.[Li].[CH3:18][C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([CH3:28])[CH:27]=1)[CH2:22][Mg]Cl>C1(C)C=CC=CC=1.O1CCCC1>[CH3:18][C:19]1[CH:20]=[C:21]([CH2:22][CH:6]([NH2:10])[C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[CH:25]=[C:26]([CH3:28])[CH:27]=1Participants
Procedure
A solution of thiophene-2-carbaldehyde (2.24 g) in anhydrous toluene was cooled to 0° C. under nitrogen inert-gas atmosphere and a solution of lithium hexamethyldisilazane (LiHMDS, 22 ml, 1.1 equiv.) was added via cannula over a 30 min period. The reaction mixture was allowed to warm up to room temperature for 2 h. After cooling to 0° C. again a solution of 3,5-dimethylbenzylmagnesium chloride (50 ml, ca. 1.5 equiv.) in tetrahydrofuran (THF) was added within 10 min and the reaction mixture allowed to warm up to room temperature and stirring continued for 3 h. This solution was quenched with aqueous potassium carbonate solution (5%) and extracted with diethyl ether. The dried and concentrated ether extracts were purified by column chromatography to give the product (1.4 g) as a yellowish oil in 30% yield.
Workup
- additionwas added within 10 min
- temperatureto warm up to room temperature
- customThis solution was quenched with aqueous potassium carbonate solution (5%)
- extractionextracted with diethyl ether
- customThe dried
- customconcentrated ether extracts were purified by column chromatography
Sources & evidence
- ORD record
- ord-28839ffa7eee42848594b15274849f23
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07989394B2
Reaction notes
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