N,N,N',N'-Tetramethylazodicarboxamide → 2-[2-(2-Benzyloxyethoxy)ethoxy]benzonitrile
Reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22]O)=[CH:12][CH:11]=1.N(C(N(C)C)=O)=NC(N(C)C)=O.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:16]([O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[C:13]1[CH:14]=[CH:15][CH:10]=[CH:11][CH:12]=1Participants
Procedure
2-Hydroxybenzonitrile (300 mg, 2.52 mmol), di(ethylene glycol) benzyl ether (593 mg, 3.02 mmol), and 1,1′-azobis(N,N-dimethylformamide) (867 mg, 5.04 mmol) were dissolved in toluene (15 ml). Thereafter, tri-n-butylphosphine (1.26 ml, 5.04 mmol) was added at 20° C. to the obtained solution, and the obtained mixture was stirred at the same above temperature for 2 hours. The generated precipitate was filtrated, and the filtrate was then diluted with ethyl acetate (20 ml). The ethyl acetate solution was washed with water twice, and then with a saturated saline solution once. The resultant was dried over anhydrous sodium sulfate, and was then concentrated under reduced pressure. The obtained pale brown oil product was purified by silica gel column chromatography (dichloromethane), so as to obtain 2-[2-(2-benzyloxyethoxy)ethoxy]benzonitrile (529 mg, 71%) in the form of a colorless oil product.
Workup
- filtrationThe generated precipitate was filtrated
- additionthe filtrate was then diluted with ethyl acetate (20 ml)
- washThe ethyl acetate solution was washed with water twice
- dry with materialThe resultant was dried over anhydrous sodium sulfate
- concentrationwas then concentrated under reduced pressure
- customThe obtained pale brown oil product was purified by silica gel column chromatography (dichloromethane)
Sources & evidence
- ORD record
- ord-2f61d2458c2e40978e99b1bfd18fbc5a
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820693B2
Reaction notes
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