Pyridine → Tos-PEG4-t-butyl ester
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].[C:20]1(C)[C:21]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:23]=[CH:24][CH:25]=1.N1C=CC=C[CH:32]=1>>[S:26]([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:21]1[CH:20]=[CH:25][C:24]([CH3:32])=[CH:23][CH:22]=1)(=[O:27])=[O:28]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
Into a 250-mL round-bottom flask, was placed a solution of tert-butyl 3-(2-(2-(2-hydroxyethoxyl)ethoxy)ethoxy)propanoate (10 g, 35.97 mmol, 1.00 equiv) in pyridine (40 mL). This was followed by the addition of toluenesulfonyl 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. The resulting mixture was concentrated under vacuum. The residue was dissolved in 30 mL of dichloromethane. The resulting mixture was washed with 3×20 mL of 3% hydrochloric acid (aq) and 20 mL of brine. The mixture was dried over sodium sulfate and concentrated under vacuum to give 14 g (90%) of tert-butyl 3-(2-(2-(2-(tosyloxy)ethoxy)ethoxy)ethoxy)propanoate as yellow oil.
Workup
- customInto a 250-mL round-bottom flask, was placed
- concentrationThe resulting mixture was concentrated under vacuum
- dissolutionThe residue was dissolved in 30 mL of dichloromethane
- washThe resulting mixture was washed with 3×20 mL of 3% hydrochloric acid (aq) and 20 mL of brine
- dry with materialThe mixture was dried over sodium sulfate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-7af2a43900874426af25c94cd5ab0a2c
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09289430B2
Reaction notes
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