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

HRID 926795Notes

Reaction equation

HRID 926795 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-trioxadodecanoate

Product 1

HCID 60146205Tos-PEG4-t-butyl esterYield 90.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To tert-butyl 3-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)propanoate (10 g, 35.97 mmol, 1.00 equiv) in pyridine (40 mL) was added 4-methylbenzene-1-sulfonyl chloride (6.8 g, 35.79 mmol, 1.00 equiv), in portions at 0° C. The resulting solution was stirred for 4 h at 0° C. and then concentrated under vacuum. The residue was dissolved in 30 mL of dichloromethane, washed with 3×20 mL of 3% hydrochloric acid (aq) and 20 mL of brine, and then dried over sodium sulfate. The solution was concentrated under vacuum to afford 14 g (90%) of tert-butyl 3-(2-(2-(2-(tosyloxy)ethoxy)ethoxy)ethoxy)propanoate as a yellow oil.

Workup

  1. customat 0° C
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in 30 mL of dichloromethane
  4. washwashed with 3×20 mL of 3% hydrochloric acid (aq) and 20 mL of brine
  5. dry with materialdried over sodium sulfate
  6. concentrationThe solution was concentrated under vacuum

Sources & evidence

ORD record
ord-1bba5df8e35a49a088ae3dd9ad4405bc
Source dataset
uspto-grants-2016_03
Patent number
US09289429B2

Reaction notes

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