Glycolaldehyde → trans-2-Acetoxymethyl-5-acetoxy-1,3-oxathiolane
Reaction equation
[CH2:1]([OH:4])[CH:2]=O.[CH2:5]1[S:10][CH:9]([OH:11])[CH2:8]S[CH:6]1[OH:12].[C:13](Cl)(=[O:15])[CH3:14].C([O-])(O)=[O:18].[Na+]>N1C=CC=CC=1>[C:13]([O:15][CH2:8][C@H:9]1[S:10][CH2:5][C@H:6]([O:12][C:1](=[O:4])[CH3:2])[O:11]1)(=[O:18])[CH3:14]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of glycoaldehyde (1.2 g, 0.01 mol) and mercaptoacetaldehyde dimer (1.52 g, 0.01 mol) in dry pyridine (20 ml) was heated at 90° C. for 2 h. The clear solution was then cooled in an ice-bath to 0° C., followed by adding acetyl chloride (2.8 ml). The mixture was stirred at room temperature overnight (16 h), and poured into saturated aqueous NaHCO3 solution (100 ml). The product was extracted into methylene chloride (3×100 ml), washed with water (2×100 ml), dried over MgSO4 and filtered. The solvent was removed on an evaporator and the oily residue was purified on silica gel hexane:EtOAc 9:1 as eluant to give the product (2.8 g) in 59% yield as a mixture of 1:1 cis:trans isomers.
Workup
- temperatureThe clear solution was then cooled in an ice-bath to 0° C.
- extractionThe product was extracted into methylene chloride (3×100 ml)
- washwashed with water (2×100 ml)
- dry with materialdried over MgSO4
- filtrationfiltered
- customThe solvent was removed on an evaporator
- customthe oily residue was purified on silica gel hexane:EtOAc 9:1 as eluant
Sources & evidence
- ORD record
- ord-bf3d8002e26a46769f34eb6d3fb4c9a8
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06175008B1
Reaction notes
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