Dimethylformamide → 4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-3-tricyclo[3.3.1.13,7]dec-1-ylbenzaldehyde
Reaction equation
[Mg].Br[CH:3](Br)C.[C:6]12([C:16]3[C:17]([O:27][SiH:28]([CH3:30])[CH3:29])=[C:18](Br)[CH:19]=[CH:20][C:21]=3C(C)(C)C)[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2.CN([CH:34]=[O:35])C.[CH2:36]1[CH2:40]OC[CH2:37]1>>[Si:28]([O:27][C:17]1[CH:18]=[CH:19][C:20]([CH:34]=[O:35])=[CH:21][C:16]=1[C:6]12[CH2:13][CH:12]3[CH2:11][CH:10]([CH2:9][CH:8]([CH2:14]3)[CH2:7]1)[CH2:15]2)([C:36]([CH3:37])([CH3:40])[CH3:3])([CH3:29])[CH3:30]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
2.6 g of magnesium and 0.05 ml of dibromoethane are added to 33 g (78 mmol) of 3-(1-adamantyl)-4-tertbutyldimethylsilyloxybromobenzene in 300 ml of THF and then the mixture is refluxed for 3 h 30 min under nitrogen After cooling the mixture to 0° C., 5.8 ml of anhydrous DMF are then added and the mixture is left stirring for 1 h at room temperature. After evaporation, the residue is taken up in 100 ml of water, acidified up to pH 5, extracted with ether and the organic phase is washed with water and dried over magnesium sulphate. 22.3 g (77%) of the expected derivative are isolated, which derivative melts at 121°-122° C.
Workup
- temperaturethe mixture is refluxed for 3 h 30 min under nitrogen
- waitthe mixture is left
- customAfter evaporation
- extractionextracted with ether
- washthe organic phase is washed with water
- dry with materialdried over magnesium sulphate
- custom22.3 g (77%) of the expected derivative are isolated
Sources & evidence
- ORD record
- ord-ab858c15d9364944b08c22171dfc1a48
- Source dataset
- uspto-grants-1996_08
- Patent number
- US05547983
Reaction notes
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