Water → 2-(Tetrahydro-2-thienyl)pyridine

HRID 1680186Notes

Reaction equation

HRID 1680186 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.CN(P(N(C)C)(N(C)C)=O)C.O.C(OCC)C>O1CCCC1>[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH:6]1[CH2:2][CH2:3][CH2:4][S:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 12679HexamethylphosphoramideHCID 12893092HCID 12893092, compound

Product 1

HCID 30186712-(Tetrahydro-2-thienyl)pyridineYield 69.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of pyrid-2-ylmethyl 3-chloropropyl sulphide (330 g) in anhydrous tetrahydrofuran (400 cc) is added dropwise, in the course of 20 minutes, at a temperature of about 25° C., to a solution of potassium tert.-butylate (283 g) in a mixture of anhydrous hexamethylphosphorotriamide (428 cc) and anhydrous tetrahydrofuran (2300 cc). After stirring for 1 hour, the reaction mixture is added to a mixture of distilled water (4200 cc) and diethyl ether (2500 cc). After decantation, the aqueous phase is again extracted with diethyl ether (1700 cc). The combined ether extracts are washed three times with distilled water (12600 cc in total), dried over anhydrous sodium sulphate and concentrated to dryness. 2-(Pyrid-2-yl)-tetrahydrothiophene (189 g) is thus obtained in the form of a brown oil [Rf=0.56; chromatography on a thin layer of silica gel; solvent: ethyl acetate-cyclohexane (50:50 by volume)].

Workup

  1. extractionAfter decantation, the aqueous phase is again extracted with diethyl ether (1700 cc)
  2. washThe combined ether extracts are washed three times with distilled water (12600 cc in total)
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-140ddf91978b477abdabbd8d2854ff07
Source dataset
uspto-grants-1981_06
Patent number
US04272534

Reaction notes

Loading…