Water → 3-(Thiolan-2-yl)pyridine
Reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5][CH2:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.CC(C)([O-])C.[K+].CN(P(N(C)C)(N(C)C)=O)C.O>O1CCCC1.C(OCC)C>[N:9]1[CH:10]=[CH:11][CH:12]=[C:7]([CH:6]2[CH2:2][CH2:3][CH2:4][S:5]2)[CH:8]=1Participants
Conditions
- Temperature
- 20 °C
Procedure
A solution of pyrid-3-yl-methyl 3-chloropropyl sulphide (59 g) in anhydrous tetrahydrofuran (75 cc) is added dropwise, in the course of 15 minutes and whilst keeping the temperature below 32° C. to a solution of potassium tert.-butoxide (50.8 g) in a mixture of anhydrous hexamethylphosphorotriamide (77 cc) and anhydrous tetrahydrofuran (410 cc). After stirring for 1 hour at a temperature of about 20° C. the reaction mixture is added to a mixture of distilled water (750 cc) and diethyl ether (420 cc). After decantation, the aqueous phase is re-extracted with diethyl ether (200 cc). The combined ether phases are washed three times with distilled water (2100 cc in total), dried over anhydrous magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 45° C. 2-(Pyrid-3-yl)-tetrahydrothiophen (30 g) is thus obtained in the form of a brown oil.
Workup
- customthe temperature below 32° C.
- extractionAfter decantation, the aqueous phase is re-extracted with diethyl ether (200 cc)
- washThe combined ether phases are washed three times with distilled water (2100 cc in total)
- dry with materialdried over anhydrous magnesium sulphate
- filtrationfiltered
- concentrationthe filtrate is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 45° C
Sources & evidence
- ORD record
- ord-fffc139a798e472c84b2e02dbe34f483
- Source dataset
- uspto-grants-1983_04
- Patent number
- US04379154
Reaction notes
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