Water → HCID 10703784, compound

HRID 1584868Notes

Reaction equation

HRID 1584868 reaction equation
C1(C)C=CC(S(O[CH2:11][C@@H:12]2[O:14][CH2:13]2)(=O)=O)=CC=1.[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([OH:25])=[C:21]([CH:24]=1)[CH:22]=[O:23].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([O:25][CH2:11][C@@H:12]2[O:14][CH2:13]2)=[C:21]([CH:24]=1)[CH:22]=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 154187Glycidyl tosylate, (R)-

Product 1

HCID 10703784HCID 10703784, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (R)-glycidyl 4-toluenesulphonate (10.0 g), 5-chloro-2-hydroxybenzaldehyde (8.92 g) and potassium carbonate (7.87 g) in dimethylformamide (200 ml) was stirred and heated at 60° C. for 5 hours then allowed to stand for 18 hours. Water (200 ml) was added and the resultant mixture extracted with ether (3×150 ml). The combined ether extracts were washed with brine (3×150 ml), dried over magnesium sulphate and the solvent evaporated. The oily residue was purified by flash chromatography on silica eluting with a 25:1 followed by a 10:1 mixture of petroleum ether (b.p. 40-60° C.) and ethyl acetate to give (R)-5-chloro-2-(2,3-epoxypropoxy)benzaldehyde (8.1 g) contaminated with ~10% of an unknown impurity, which was used without further purification.

Workup

  1. extractionthe resultant mixture extracted with ether (3×150 ml)
  2. washThe combined ether extracts were washed with brine (3×150 ml)
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent evaporated
  5. customThe oily residue was purified by flash chromatography on silica eluting with a 25:1
  6. additionfollowed by a 10:1 mixture of petroleum ether (b.p. 40-60° C.) and ethyl acetate

Sources & evidence

ORD record
ord-fe09161b5ba148f0951e9e14a62292d9
Source dataset
uspto-grants-1999_08
Patent number
US05935973

Reaction notes

Loading…