4-Toluenesulfonyl chloride → Tos-PEG4-t-butyl ester

HRID 870217Notes

Reaction equation

HRID 870217 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>N1C=CC=CC=1>[S:27]([O:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([C:24]1[CH:25]=[CH:26][C:21]([CH3:20])=[CH:22][CH:23]=1)(=[O:29])=[O:28]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 3625858tert-Butyl 12-hydroxy-4,7,10-trioxadodecanoate2×

Product 1

HCID 60146205Tos-PEG4-t-butyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of tert-butyl 3-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)propanoate (intermediate 179.1) (9.6 g, 34.49 mmol, 1.00 equiv) in anhydrous pyridine (12 mL). The mixture was cooled to 0° C. and 4-methylbenzene-1-sulfonyl chloride (7.9 g, 41.44 mmol, 1.20 equiv) was added slowly in several portions. The resulting solution was stirred at 0° C. for 1-2 h and then the flask containing the reaction mixture was sealed and placed in a refrigerator at 0° C. overnight. The mixture was poured into 120 mL of water/ice, and the aqueous layer was extracted with 3×50 mL of DCM. The combined organic layers were washed with 2×50 mL of cold 1.0 N hydrogen chloride and saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum to yield 13.4 g (90%) of tert-butyl 3-(2-(2-(2-(tosyloxy)ethoxy)ethoxy)ethoxy)propanoate as pale yellow oil.

Workup

  1. customInto a 250-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. additionthe flask containing the reaction mixture
  4. customwas sealed
  5. waitplaced in a refrigerator at 0° C. overnight
  6. extractionthe aqueous layer was extracted with 3×50 mL of DCM
  7. washThe combined organic layers were washed with 2×50 mL of cold 1.0 N hydrogen chloride and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-e1b82a32f8034d8d8a98be1601444274
Source dataset
uspto-grants-2015_03
Patent number
US08969377B2

Reaction notes

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