Ethyl 5-(2-phenyleth-1-ynyl)nicotinate → (E)-(5-Styrylpyridin-3-yl)-methanol

HRID 606942노트

반응식

HRID 606942 반응식
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[N:7][CH:6]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:11](/[C:9]1[CH:10]=[C:5]([CH2:4][OH:3])[CH:6]=[N:7][CH:8]=1)=[CH:12]\[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

4

반응물 2

HCID 2779231Ethyl 5-(2-phenyleth-1-ynyl)nicotinateHCID 21226445Aluminium lithium hydride2회

생성물 1

HCID 67047921(E)-(5-Styrylpyridin-3-yl)-methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Add a solution of commercially available 5-phenylethynyl-nicotinic acid ethyl ester (0.4 g, 1.59 mmol) in dry tetrahydrofuran (20 mL) to a solution of lithium aluminum hydride (20 mL, 0.08 M in tetrahydrofuran) at room temperature under nitrogen and stir for 3 h. Add a solution of lithium aluminum hydride (2 mL, 1 M in tetrahydrofuran) and stir for 1 h. Slowly add methanol (2 mL) and concentrate. Dilute with ethyl acetate, wash with water and a saturated aqueous solution of sodium chloride and dry. Purify the residue by silica gel chromatography, eluting with 5:1 hexanes:ethyl acetate to 10:90 hexanes:ethyl acetate, to give the E-isomer (7 mg, 2%).

후처리

  1. stirringstir for 1 h
  2. concentrationSlowly add methanol (2 mL) and concentrate
  3. additionDilute with ethyl acetate
  4. washwash with water
  5. dry with materiala saturated aqueous solution of sodium chloride and dry
  6. customPurify the residue by silica gel chromatography
  7. washeluting with 5:1 hexanes
  8. customethyl acetate to 10:90 hexanes:ethyl acetate, to give the E-isomer (7 mg, 2%)

출처 및 근거

ORD 기록
ord-884ac9bbc70846c6bf63329f3c45c4f2
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915424B2

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