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

HRID 1680186노트

반응식

HRID 1680186 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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)].

후처리

  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

출처 및 근거

ORD 기록
ord-140ddf91978b477abdabbd8d2854ff07
출처 데이터셋
uspto-grants-1981_06
특허 번호
US04272534

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