Reaction equation
[C:1]1([CH:7]([OH:11])[CH2:8][CH:9]=[CH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN([CH2:17][CH3:18])CC.Cl[SiH2:20][CH:21]=C(C)C.[CH2:25](Cl)Cl>>[CH3:25][SiH:20]([CH3:21])[CH:17]=[CH:18][O:11][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][CH:9]=[CH2:10]Participants
5
Procedure
In a 50-mL flask was placed 1-phenyl-3-buten-1-ol (3.19 g, 21.5 mmol) and Et3N (4.48 mL, 32.25 mmol, 1.5 equiv) in CH2Cl2 (30 mL) under N2 atmosphere at 0° C. (ice bath temperature). To the mixture was added dropwise with chlorodimethylvinylsilane (3.86 mL, 28.0 mmol, 1.2 equiv). The mixture was allowed to warm to room temperature and was stirred for 2 h. The mixture was then poured to ice water (30 mL) and 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 distilled under reduced pressure to afford 4.59 g (92%) of 73 as a colorless liquid.
Workup
- customIn a 50-mL flask was placed
- customat 0° C.
- extractionwas extracted with CH2Cl2 (2×30 mL)
- dry with materialThe combined organic layers were dried (Na2SO4)
- filtrationfiltered
- customthe solvent was removed by rotary evaporation
- distillationThe residue was distilled under reduced pressure
Sources & evidence
- ORD record
- ord-904b5d5a4ba1444b8fb990e0f257c336
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06867323B2
Linked notes
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