Water → 5-(4,4,5,5,5-Pentafluoropentylsulfinyl)pentanal
Reaction equation
C[O:2][CH:3](OC)[CH2:4][CH2:5][CH2:6][CH2:7][S:8]([CH2:10][CH2:11][CH2:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[O:9].C(O)(C(F)(F)F)=O.O.CCCCCC>C(Cl)(Cl)Cl.C(OCC)(=O)C>[F:19][C:13]([F:18])([C:14]([F:15])([F:16])[F:17])[CH2:12][CH2:11][CH2:10][S:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[O:2])=[O:9]Participants
7
Procedure
5,5-Dimethoxy-1-(4,4,5,5,5-pentafluoropentylsulfinyl)pentane (355 mg, 0.10 mmol) was dissolved in chloroform (2 ml), 50% TFA aqueous solution (2 ml) was added thereto at room temperature, and the resulting mixture was then stirred for 2 hours. After the reaction was completed, the reaction solution was poured into water and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a crude product. This crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=2:1→1:1-ethyl acetate) to give 5-(4,4,5,5,5-pentafluoropentylsulfinyl)pentanal (28 mg, yield 93%).
Workup
- extractionextracted with chloroform
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customto give a crude product
- customThis crude product thus obtained
Sources & evidence
- ORD record
- ord-c82084f26390484a87066af56670b886
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07074819B2
Reaction notes
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