Hydrochloric Acid → 3-[(Thiophen-2-yl)methyl]pyridine

HRID 52183

반응식

HRID 52183 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7](O)[C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:2]=1.O.O.[Sn](Cl)Cl.Cl>C(O)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:2]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 650499Pyridin-3-yl(thiophen-2-yl)methanol

생성물 1

HCID 132871183-[(Thiophen-2-yl)methyl]pyridine수율 32.5%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a solution of 2-(3-pyridylhydroxymethyl)thiophene (8.82 g, 46.2 mmol), prepared as in step 1, in acetic acid (50 mL) was added tin(II)chloride dihydrate (22.9 g, 101 mmol) and HCl gas was bubbled through the reaction mixture for about 10 min. The reaction mixture was stirred for 1.5 hours at ambient temperature, and the liquid was decanted, concentrated in vacuo to a volume of about 10 mL, and poured into H2O. The aqueous solution was made basic by the slow addition of saturated aqueous NaHCO3 and extracted with ethyl acetate/ether. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica gel (5% methanol/CHCl3) gave 2-(3-pyridylmethyl)thiophene (2.63 g).

후처리

  1. customwas bubbled through the reaction mixture for about 10 min
  2. customthe liquid was decanted
  3. concentrationconcentrated in vacuo to a volume of about 10 mL
  4. additionpoured into H2O
  5. additionThe aqueous solution was made basic by the slow addition of saturated aqueous NaHCO3
  6. extractionextracted with ethyl acetate/ether
  7. dry with materialThe organic phase was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-54f8447cc7e34580a563ab32a593e469
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616596

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