Acetone → 6,7-Dichloro-5-hydroxy-alpha,alpha-dimethylbenzo[b]thiophene-2-methanol
Reaction equation
[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[C:10]=1[Cl:11].C([Li])CCC.C(Cl)(Cl)(Cl)Cl.C(=O)=O.[CH3:26][C:27]([CH3:29])=[O:28]>O1CCCC1.C(O)(=O)C.O>[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[CH:9]=[C:8]([C:27]([CH3:29])([CH3:26])[OH:28])[S:7][C:6]=2[C:10]=1[Cl:11]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 6,7-dichloro-5-hydroxybenzo[b]thiophene in 28 ml of dried tetrahydrofuran at -28° is added 21 ml of 2.5M n-butyllithium, maintaining the temperature below -18°. Following the addition, the carbon tetrachloride-dry ice bath is replaced with an ice-water bath and the mixture is stirred at 0°-5° for about 4 hrs. A solution of 3.3 ml of acetone in 10 ml tetrahydrofuran is added dropwise. After stirring for one hr, the solution is poured onto 100 ml of water and acidified to pH=5-6 with glacial acetic acid. The acidic solution is extracted with ethyl acetate, washed, dried over anhydrous magnesium sulfate, filtered and the solvent is removed to give 3.84 g of 6,7-dichloro-5-hydroxy-α,α-dimethylbenzo[b]thiophene-2-methanol, mp 171°-173°.
Workup
- temperaturemaintaining the temperature below -18°
- additionthe addition
- stirringAfter stirring for one hr
- extractionThe acidic solution is extracted with ethyl acetate
- washwashed
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe solvent is removed
Sources & evidence
- ORD record
- ord-48c5aeaa65d448eba21da4ea29936087
- Source dataset
- uspto-grants-1987_06
- Patent number
- US04672138
Reaction notes
Loading…