Hydrochloric Acid → 2-((Tert-butyldimethylsilyl)oxy)acetaldehyde
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]([Si:15]([CH3:21])([CH3:20])[O:16][CH2:17][CH2:18][OH:19])([CH3:14])[CH3:13].Cl>ClCCl.C(N(CC)CC)C.N1C=CC=CC=1>[CH3:14][C:12]([Si:15]([CH3:21])([CH3:20])[O:16][CH2:17][CH:18]=[O:19])([CH3:11])[CH3:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -70 °C
Procedure
Under nitrogen and with stirring, 4.71 ml of oxalyl chloride were dissolved in 120 ml of dichloromethane and the solution was cooled to -70° C. Over 12 minutes while maintaining the temperature at -65° C., a solution of 8 ml of dimethylsulfoxide and 26 ml of dichloromethane was introduced. Then, after 10 minutes of contact at this temperature, a solution of 8.81 g of the product of Step A, 50 ml of dichloromethane and 8.86 ml of pyridine was added over 12 minutes at -65° C. After 15 minutes of contact at this temperature, 35 ml of triethylamine were added over 8 minutes at -65° C. At +13° C., the pH was adjusted to 4 by adding N hydrochloric acid. After decanting, re-extracting with 50 ml of dichloromethane, drying the organic phase and distilling under reduced pressure, the crude product obtained was chromatographed over silica and eluted with dichloromethane to obtain 7.95 g of 2-[(1,1-dimethylethyl)dimethylsilyloxy]-acetaldehyde.
Workup
- temperatureOver 12 minutes while maintaining the temperature at -65° C.
- customAt +13° C.
- customAfter decanting
- extractionre-extracting with 50 ml of dichloromethane
- customdrying the organic phase
- distillationdistilling under reduced pressure
- customthe crude product obtained
- customwas chromatographed over silica
- washeluted with dichloromethane
Sources & evidence
- ORD record
- ord-1a3faf8fc76f4b03802eedfb88b99191
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05385897
Reaction notes
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