1,2-Dimethoxyethane → HCID 12790261, compound

HRID 848425Notes

Reaction equation

HRID 848425 reaction equation
N(=[C:3]1[C:9]([CH3:11])([CH3:10])[CH:8]2[C:5]([CH3:13])([CH2:6][CH:7]2[OH:12])[CH2:4]1)O.C(COC)[O:15]C>O.[Cl-].[Cl-].[Cl-].[Ti+3]>[CH3:13][C:5]12[CH2:6][CH:7]([OH:12])[CH:8]1[C:9]([CH3:11])([CH3:10])[C:3](=[O:15])[CH2:4]2

Participants

5

Reactant 2

HCID 80711,2-DimethoxyethaneHCID 86738041HCID 86738041, compound

Product 1

HCID 12790261HCID 12790261, compound

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 962WaterSolvent2×

Procedure

To a solution of 600 mg of the oxime (V) in a mixture of 10 ml of dimethoxyethane and 5 ml of water, was added 6 ml of 16% titanium trichloride and the mixture was kept at 50° to 60° C. for 30 minutes under an argon atmosphere. After cooling, the mixture was admixed with 20 ml of water and extracted with methylene chloride. The extract was washed with an aqueous sodium bicarbonate solution, then with an aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo to give 425 mg of an oil. This oil was chromatographed over silica gel to give 305 mg of an oil (IV): nD20 1.4787; MS: m/e 168 (M+).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with methylene chloride
  3. washThe extract was washed with an aqueous sodium bicarbonate solution
  4. dry with materialwith an aqueous sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee0d561e59244332b3e4e8486cac0721
Source dataset
uspto-grants-1981_10
Patent number
US04296036

Reaction notes

Loading…