Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[OH:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20](O)[C:16]=1[C:17]([O-:19])=[O:18].[C:25]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>>[C:9]([O:8][C:7]([NH:6][CH2:5][CH2:4][CH2:3][CH2:2][O:1][C:20]1[CH:21]=[CH:22][CH:23]=[C:15]([OH:14])[C:16]=1[C:17]([O:19][CH3:25])=[O:18])=[O:13])([CH3:10])([CH3:12])[CH3:11]Participants
5
Procedure
To a round bottom flask was charged with tert-butyl 4-hydroxybutylcarbamate (400 mg, 2.1 mmol), 463 mg of 2,6-dihydroxybenzoate (463 mg, 2.7 mmol), and triphenylphosphine (777 mg, 3.0 mmol). The flask was vacuumed and back flushed with nitrogen (3×), capped with a rubber septum, and kept under positive nitrogen atmosphere. THF (anhydrous) was then added, followed by dropwise addition of DEAD (433 μL, 2.7 mmol). Most of the starting material was consumed within the first 30 min. Solvent was then removed in vacuo, and the residue was purified on a silica gel chromatography eluting with 15-30% EtOAc in hexane to give the ether product (410 mg, 57%) as a cloroless oil.
Workup
- customback flushed with nitrogen (3×)
- customcapped with a rubber septum
- additionTHF (anhydrous) was then added
- customMost of the starting material was consumed within the first 30 min
- customSolvent was then removed in vacuo
- customthe residue was purified on a silica gel chromatography
- washeluting with 15-30% EtOAc in hexane
- customto give the ether product (410 mg, 57%) as a cloroless oil
Sources & evidence
- ORD record
- ord-34878e310ca74234ace5aadad2a82f99
- Source dataset
- uspto-grants-2005_12
- Patent number
- US06972340B2
Linked notes
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