Triethylamine → 4-Hydroxymethyl-2-(3,4,5-trimethoxyphenyl-ethynyl)pyridine

HRID 1634900노트

반응식

HRID 1634900 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]#[C:14][C:15]2[CH:20]=[C:19]([C:21](O)=[O:22])[CH:18]=[CH:17][N:16]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(N(CC)CC)C.ClC(OCC)=O.C(OCC)(=O)C>C1COCC1>[OH:22][CH2:21][C:19]1[CH:18]=[CH:17][N:16]=[C:15]([C:14]#[C:13][C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:20]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10928Ethyl chloroformateHCID 186750082-(3,4,5-Trimethoxyphenylethynyl)pyridine-4-carboxylic Acid

생성물 1

HCID 186749764-Hydroxymethyl-2-(3,4,5-trimethoxyphenyl-ethynyl)pyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2-(3,4,5-Trimethoxyphenylethynyl)pyridine-4-carboxylic acid (90 mg) was dissolved in THF (6 mL), and to the solution triethylamine (35 mg) was added at 0° C. under an argon atmosphere. Ethyl chloroformate (34 mg) was then added to the mixture, and the mixture was stirred for 1 hour. Ethyl acetate was added to the reaction mixture, and the mixture was washed with water and saturated brine and dried over anhydrous sodium sulfate. After concentrating the reaction mixture, the residue was dissolved in THF (2 mL), and to the solution an aqueous solution (1 mL) of sodium borohydride (16 mg) was added at 0° C., and the resultant mixture was stirred for 1 hour. The reaction mixture was extracted with ethyl acetate, and the resultant organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After concentrating the organic layer under reduced pressure, the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1 to ethyl acetate) to obtain the title compound.

후처리

  1. washthe mixture was washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationAfter concentrating the reaction mixture
  4. dissolutionthe residue was dissolved in THF (2 mL)
  5. additionto the solution an aqueous solution (1 mL) of sodium borohydride (16 mg) was added at 0° C.
  6. stirringthe resultant mixture was stirred for 1 hour
  7. extractionThe reaction mixture was extracted with ethyl acetate
  8. washthe resultant organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationAfter concentrating the organic layer under reduced pressure
  11. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1 to ethyl acetate)

출처 및 근거

ORD 기록
ord-a4eadff269a34244bbd624bf318589af
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06509329B1

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