Citric Acid → trans-5-Tert-butoxycarbonyl-2-formylmethyltetrahydrothiophene
Reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[S:12][C@@H:11]([CH2:13][C:14]#N)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:19]>C(OCC)C.[H-].C([Al+]CC(C)C)C(C)C.CCCCCC>[C:1]([O:5][C:6]([C@@H:8]1[S:12][C@@H:11]([CH2:13][CH:14]=[O:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
To a stirred solution of trans-5-tert-butoxycarbonyl-2-cyanomethyltetrahydrothiophene (2.3 g) in diethylether (100 ml), 1M diisobutyl-aluminiumhydride dissolved in hexane (12.1 ml) is added at -30° C. and the mixture is stirred for 2 hours at -20°--10° C. 10% aqueous citric acid solution is added to the mixture and extracted with ethyl acetate - benzene (1:1). The organic layer is washed with 10% aqueous citric acid solution, water and saturated sodium chloride solution. The organic layer is dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give trans-5-tert-butoxycarbonyl-2-formylmethyltetrahydrothiophene.
Workup
- additionis added at -30° C.
- extractionextracted with ethyl acetate - benzene (1:1)
- washThe organic layer is washed with 10% aqueous citric acid solution, water and saturated sodium chloride solution
- dry with materialThe organic layer is dried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customThe oily residue was purified by a silica gel column chromatography
Sources & evidence
- ORD record
- ord-48084e79c97c4cf49d2754da00dbc006
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05292767
Reaction notes
Loading…