Reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][CH:6]=1.CCCCC.C([Li])(C)(C)C.CN([CH:30]=[O:31])C.C(OCC)(=O)C>C(OCC)C.O>[CH3:15][Si:13]([CH3:14])([CH3:16])[C:12]#[C:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][O:2][CH3:1])=[C:6]([CH:7]=1)[CH:30]=[O:31]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 4-(2-trimethylsilylethynyl)phenol methoxymethyl ether (6.08 g) in diethyl ether (450 ml) was cooled to -78° C., to which was added dropwise, under argon atmosphere, a 1.7M t-butyl lithium pentane solution (18 ml), and the mixture was stirred for one hour at the same temperature. To the reaction mixture was then added dropwise DMF(5 ml), followed by warming up to room temperature and stirring overnight. To the reaction mixture were added ethyl acetate and water, which was subjected to extraction. The organic layer was washed (a saturated aqueous saline solution) and dried (anhydrous magnesium sulfate), followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 5-(2-trimethylsilylethynyl)-2-methoxymethoxybenzaldehyde (5.29 g) (Compound B-27). The physical properties are shown in Table 8.
Workup
- additionwas added dropwise, under argon atmosphere
- extractionwas subjected to extraction
- washThe organic layer was washed (a saturated aqueous saline solution) and
- dry with materialdried (anhydrous magnesium sulfate)
- distillationby distilling off the solvent under reduced pressure
- customThe residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-01eb2cf2a43c4d479d27f41b864bad98
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05716971
Linked notes
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