Water → 2-(2-hydroxyethyl)-N-(1,1-dimethylethyl)benzenesulfonamide
Reaction equation
[CH3:1][C:2]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].C([Li])CCC.[CH2:20]1[O:22][CH2:21]1.O>O1CCCC1>[OH:22][CH2:21][CH2:20][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[S:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])(=[O:8])=[O:7]Participants
Procedure
A solution of N-(1,1-dimethylethyl)benzenesulfonamide (40.0 g) in 550 ml dry tetrahydrofuran was cooled to 0° and 250 ml of 1.6M n-butyllithium added dropwise at 0°. After the addition of one equivalent of base, the solution turned yellow. After stirring for 2 hours at room temperature, the resulting suspension was cooled to 0° and 13 ml of ethylene oxide added dropwise. After stirring for 3.5 hours at room temperature, the homogeneous yellow solution was poured into water. The product was extracted with ether and dried (Na2SO4). Concentration gave a yellow oil which was purified by column chromatography [400 g silica gel, ether/hexane (1:1) followed by ethyl acetate]. Pure 2-(2-hydroxyethyl)-N-(1,1-dimethylethyl)benzenesulfonamide was obtained as a colorless oil which solidified after several days; m.p. 43°-45°.
Workup
- temperaturethe resulting suspension was cooled to 0°
- stirringAfter stirring for 3.5 hours at room temperature
- extractionThe product was extracted with ether
- dry with materialdried (Na2SO4)
- concentrationConcentration
- customgave a yellow oil which
- customwas purified by column chromatography [400 g silica gel, ether/hexane (1:1) followed by ethyl acetate]
Sources & evidence
- ORD record
- ord-c0a5f3abeff142799fde8ef16c5089c6
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04662933
Reaction notes
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