Reaction equation
[Si:1]([O:8][CH2:9][C:10]1[S:11][S:12][C:13]([CH2:16][OH:17])=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O>C1COCC1>[Si:1]([O:8][CH2:9][C:10]1[S:11][S:12][C:13]([CH:16]=[O:17])=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-[(tert-butyldimethylsilyloxy)methyl]-6-(hydroxymethyl)-1,2-dithiin (U.S. Ser. No. 08/212,096) (600 mg, 2.07 mmol) in THF (25 mL) at 0° C. was added quickly the Dess-Martin periodinane reagent (1.20 g, 2.83 mmol) and the mixture was stirred at 0° C. for 30 min, then at room temperature for another 30 min. Upon completion of the reaction (monitored by TLC), 12 mL of H2O was added and the mixture was extracted with ether (3×). The combined organics washings were washed with H2O, sodium hydrogen carbonate (3%-soln.), brine, dried (Na2SO4) and evaporated. Flash chromatography (eluting with hexane/EtOAc 3/1) yielded 560 mg (94%) of the title aldehyde as a dark red, almost purple, crystalline compound.
Workup
- waitat room temperature for another 30 min
- additionwas added
- extractionthe mixture was extracted with ether (3×)
- washThe combined organics washings were washed with H2O, sodium hydrogen carbonate (3%-soln.), brine
- dry with materialdried (Na2SO4)
- customevaporated
- washFlash chromatography (eluting with hexane/EtOAc 3/1)
Sources & evidence
- ORD record
- ord-d08a7e6211b241ebadf1660bcca7aec2
- Source dataset
- uspto-grants-1996_12
- Patent number
- US05580897
Linked notes
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