4-Toluenesulfonyl chloride → HCID 86754920, compound

HRID 412090Notes

Reaction equation

HRID 412090 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[OH:12][CH:13]([CH2:16][N:17]=[N+:18]=[N-:19])[CH2:14]O.C(N(CC)CC)C>C(Cl)Cl.O>[OH:12][CH:13]([CH2:16][N:17]=[N+:18]=[N-:19])[CH3:14].[S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)([O-:12])(=[O:3])=[O:2]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 1082123-Azido-1,2-propanediol

Product 1

HCID 86754920HCID 86754920, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Tosyl chloride (2.3 g, 12 mmol) was added to a solution of 2-hydroxy-3-azido-propanol (1.17 g, 10 mmol) and triethyl amine (3.6 g, 36 mmol) in methylene chloride (50 ml) and was stirred at RT for 4 h. The reaction was diluted with water (20 ml), extracted with EtOAc (2×50 ml); the combined organic layers were extracted with pH 7 buffer (2×50 ml), then were dried with magnesium sulfate, filtered, concentrated in vacuo, and chromatographed (silica gel, 30% EtOAc/hexanes) to produce a white solid (1.2 g, 44%); MS(ES) M+H+=272.2.

Workup

  1. extractionextracted with EtOAc (2×50 ml)
  2. extractionthe combined organic layers were extracted with pH 7 buffer (2×50 ml)
  3. dry with materialwere dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customchromatographed (silica gel, 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-53e88fd870cc497c8661c7d0eeafe6bd
Source dataset
uspto-grants-2003_05
Patent number
US06562842B2

Reaction notes

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