2-Mercaptoethanol → 2-[2-(2-Azido-Ethoxy)-Ethylsulfanyl]-Ethanol

HRID 1521925Notes

Reaction equation

HRID 1521925 reaction equation
[OH-].[Na+].[N:3]([CH2:6][CH2:7][O:8][CH2:9][CH2:10]OS(C1C=CC(C)=CC=1)(=O)=O)=[N+:4]=[N-:5].[SH:22][CH2:23][CH2:24][OH:25]>CO>[N:3]([CH2:6][CH2:7][O:8][CH2:9][CH2:10][S:22][CH2:23][CH2:24][OH:25])=[N+:4]=[N-:5]

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 14798Sodium HydroxideHCID 600204482-(2-Azidoethoxy)ethyl 4-methylbenzenesulfonate

Product 1

HCID 866702992-[2-(2-Azido-Ethoxy)-Ethylsulfanyl]-EthanolYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous NaOH (3.33 g in 20 ml H2O, 1.5 equiv.) was added dropwise to a solution of tosylate 3 (15.8 g, 55.5 mmol) and β-mercaptoethanol (5.8 ml, 1.5 equiv.) in MeOH (200 ml). The resulting mixture was stirred at RT for 72 h then methanol was evaporated under reduced pressure. The resulting suspension was diluted with water (50 ml) and extracted with CH2Cl2 (6×50 ml). The combined organic layers were dried over MgSO4, filtrated then concentrated under reduced pressure. Purification by flash column chromatography (eluent: pet. ether/AcOEt 8:2 then 6:7) afforded sulfide 4 as a colorless liquid (8.41 g, 79%).

Workup

  1. custommethanol was evaporated under reduced pressure
  2. additionThe resulting suspension was diluted with water (50 ml)
  3. extractionextracted with CH2Cl2 (6×50 ml)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltrated
  6. concentrationthen concentrated under reduced pressure
  7. customPurification by flash column chromatography (eluent

Sources & evidence

ORD record
ord-a820e06cca8b40dfba8304f97aa6ff08
Source dataset
uspto-grants-2015_07
Patent number
US09073969B2

Reaction notes

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