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

HRID 653203Notes

Reaction equation

HRID 653203 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(C)=CC=CC=1)(=O)=O.[OH-].[Na+].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 14798Sodium 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-toluenesulphonyloxy-2-butanol are dissolved in 1 ml of ethanol and the solution is treated with 0.3 ml of alcoholic sodium 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 was dried over sodium sulphate and concentrated. There are obtained 105 mg of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-epoxybutane. M.p. 47°-48° C.

Workup

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

Sources & evidence

ORD record
ord-b01955f5f3354702a9a18122024c14c7
Source dataset
uspto-grants-1987_06
Patent number
US04675421

Reaction notes

Loading…