Hydrochloric Acid → (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1-toluenesulphonyloxy-2-butanol
Reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7](C)=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH3:12][O:13][C:14]1[C:19]([CH3:20])=[C:18]([CH3:21])[C:17]([O:22][CH3:23])=[C:16]([CH3:24])[C:15]=1[CH2:25][CH2:26][C@:27]([CH3:31])([OH:30])[CH2:28][OH:29].N1C=CC=C[CH:33]=1.Cl>C(Cl)Cl>[CH3:12][O:13][C:14]1[C:19]([CH3:20])=[C:18]([CH3:21])[C:17]([O:22][CH3:23])=[C:16]([CH3:24])[C:15]=1[CH2:25][CH2:26][C@:27]([CH3:31])([OH:30])[CH2:28][O:29][S:1]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:9][C:10]=1[CH3:33])(=[O:2])=[O:3]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
237 mg of tosyl chloride and 350 mg of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-butanediol are dissolved in 1 ml of methylene chloride. 0.180 ml of pyridine is then added dropwise at 0° C. and the mixture is left to stand at 0° C. for 1 hour and then at room temperature for 16 hours. Thereupon, 1 g of ice and 0.3 ml of concentrated hydrochloric acid are added. The mixture is then extracted with methylene chloride and the extract is dried and concentrated. There are obtained 511 mg (95%) of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1-toluylsulphonyloxy-2-butanol, [α]D20 +1.2° (c=2.6% in CHCl3).
Workup
- waitthe mixture is left
- waitat room temperature for 16 hours
- extractionThe mixture is then extracted with methylene chloride
- customthe extract is dried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-533e35f56f7b4649b1ef091a7ffdfaa5
- Source dataset
- uspto-grants-1987_08
- Patent number
- US04689427
Reaction notes
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