Dichloromethane → Dimethyl[(1-phenyl-4-pentenyl)oxy]vinylsilane
Reaction equation
[C:1]1([CH:7]([OH:12])[CH2:8][CH2:9][CH:10]=[CH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN([CH2:18][CH3:19])CC.Cl[SiH2:21][CH:22]=C(C)C.[CH2:26](Cl)Cl>>[CH3:26][SiH:21]([CH3:22])[CH:18]=[CH:19][O:12][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][CH2:9][CH:10]=[CH2:11]Participants
Procedure
In a 50-mL flask was placed 1-phenyl-4-penten-1-ol (3.24 g, 20.0 mmol) and Et3N (4.2 mL, 30.0 mmol, 1.5 equiv) in CH2Cl2 (20 mL) under a N2 atmosphere at 0° C. (internal). To the mixture was added dropwise chlorodimethylvinylsilane (3.3 mL, 24.0 mmol, 1.2 equiv). The mixture was allowed to warm to room temperature and was stirred for 0.5 h. The mixture was then poured to ice water (30 mL) and the aqueous phase was extracted with CH2Cl2 (2×30 mL). The combined organic layers were dried (Na2SO4), filtered and the solvent was removed by rotary evaporation. The residue was purified by chromatography (silica gel, hexane/EtOAc, 49/1) followed Kugelrohr distillation under reduced pressure to afford 4.48 g (91%) of F-5 as a colorless liquid.
Workup
- customIn a 50-mL flask was placed
- customat 0° C.
- extractionthe aqueous phase was extracted with CH2Cl2 (2×30 mL)
- dry with materialThe combined organic layers were dried (Na2SO4)
- filtrationfiltered
- customthe solvent was removed by rotary evaporation
- customThe residue was purified by chromatography (silica gel, hexane/EtOAc, 49/1)
- distillationKugelrohr distillation under reduced pressure
- customto afford 4.48 g (91%) of F-5 as a colorless liquid
Sources & evidence
- ORD record
- ord-46d20e41cea94e80a1766610102846f7
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06867323B2
Reaction notes
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