4-Toluenesulfonyl chloride → HCID 54385761, compound

HRID 1378527Notes

Reaction equation

HRID 1378527 reaction equation
[CH3:1][C:2]([CH2:4][C@@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])=[O:3].[S:11](Cl)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12]>N1C=CC=CC=1>[CH3:1][C:2]([CH2:4][C@@H:5]([C@@H:7]([CH2:9][O:10][S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[OH:8])[OH:6])=[O:3]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 53696787HCID 53696787, compound

Product 1

HCID 54385761HCID 54385761, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl-2-deoxy-D-ribose (8 g, 54 mmol) was dissolved in pyridine (60 mL). To this solution was added tosylchloride (10.86 g, 57 mmol) over 1 hour at 0° C. After 14 hours at room temperature, the solution was concentrated, quenched with ice water (250 mL), and extracted with ethyl acetate. The extract was washed with saturated NaHCO3, water, dried, filtered, and concentrated. The residue (13.6 g, 83.5% yield) was used directly. NMR

Workup

  1. concentrationthe solution was concentrated
  2. customquenched with ice water (250 mL)
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated NaHCO3, water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d95836ccbd144bb0b839772d6e333db0
Source dataset
uspto-grants-1997_09
Patent number
US05668152

Reaction notes

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