Dichloromethane → (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-epoxy-butane

HRID 1789603Notes

Reaction equation

HRID 1789603 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH2:14][CH2:15][C@:16]([CH3:30])([OH:29])[CH2:17]OS(C1C=CC=CC=1C)(=O)=O.[OH-].[K+].C(Cl)Cl>C(O)C>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH2:14][CH2:15][C@:16]1([CH3:30])[O:29][CH2:17]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 86740735(S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1-toluenesulphonyloxy-2-butanol

Product 1

HCID 18602184(S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-epoxy-butaneYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

177 mg of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1-toluylsulphonyloxy-2-butanol are dissolved in 1 ml of ethanol and treated with 0.3 ml of alcoholic potassium hydroxide solution (1.5N). The mixture is left to stand at room temperature for 10 minutes, 30 ml of methylene chloride are then added and the mixture is dried over anhydrous sodium sulphate and concentrated. There are obtained 105 mg of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-epoxy-butane, m.p. 47°-48° C. [α]D20 +4.91° (c=2.2% in CHCl3).

Workup

  1. waitThe mixture is left
  2. dry with materialthe mixture is dried over anhydrous sodium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c42ddd7a3bc84fa58a01dcb51e554183
Source dataset
uspto-grants-1987_08
Patent number
US04689427

Reaction notes

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