Glycolaldehyde → trans-2-Benzoyloxymethyl-5-benzoyl-1,3-oxathiolane

HRID 566525Notes

Reaction equation

HRID 566525 reaction equation
[CH2:1](O)[CH:2]=O.[CH2:5]1[S:10][CH:9](O)[CH2:8]S[CH:6]1[OH:12].[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:22]([O-:25])(O)=[O:23].[Na+]>N1C=CC=CC=1>[C:22]([O:25][CH2:8][C@H:9]1[S:10][CH2:5][C@H:6]([C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:12]1)(=[O:23])[C:2]1[CH:1]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 756GlycolaldehydeHCID 7412Benzoyl chlorideHCID 983301,4-Dithiane-2,5-diolHCID 516892Sodium Bicarbonate

Product 1

HCID 67714070trans-2-Benzoyloxymethyl-5-benzoyl-1,3-oxathiolaneYield 53%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 benzoyl chloride (4.6 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 using hexane:EtOAc 9:1 as eluant to give the product (3.65 g) in 53% yield as a mixture of 1:1 cis and trans isomers.

Workup

  1. temperatureThe clear solution was then cooled in an ice-bath to 0° C.
  2. extractionThe product was extracted into methylene chloride (3×100 ml)
  3. washwashed with water (2×100 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed on an evaporator
  7. customthe oily residue was purified on silica gel

Sources & evidence

ORD record
ord-5fd6d70eac5e4c1f9a020405bb877fe4
Source dataset
uspto-grants-2001_01
Patent number
US06175008B1

Reaction notes

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