3,4,5-Trimethoxybenzaldehyde → HCID 16110327, 화합물

HRID 273343

반응식

HRID 273343 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=[O:7].[C-:15]#[C-:16].[Na+].[Na+]>C1COCC1>[CH3:14][O:13][C:9]1[CH:8]=[C:5]([CH:6]([OH:7])[C:15]#[CH:16])[CH:4]=[C:3]([O:2][CH3:1])[C:10]=1[O:11][CH3:12]

참가 물질

4

반응물 2

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 178463197HCID 178463197, 화합물

생성물 1

HCID 16110327HCID 16110327, 화합물수율 73.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3,4,5-trimethoxybenzaldehyde (1.0 g, 5.0 mmol) in THF (50 mL) was stirred at 0° C. Sodium acetylide (18% w.t. slurry in xylene, 1.63 g, 6.1 mmol) was added via syringe. The reaction mixture was stirred overnight at room temperature and quenched by water. It was then extracted with EtOAc (30 mL×3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated to give a crude product, which was purified by flash column chromatography eluting with EtOAc/n-hexane (1:2) to afford 1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol as a white solid (815 mg, 72%).

후처리

  1. customquenched by water
  2. extractionIt was then extracted with EtOAc (30 mL×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude product, which
  8. customwas purified by flash column chromatography
  9. washeluting with EtOAc/n-hexane (1:2)

출처 및 근거

ORD 기록
ord-706fa45e5dde4051bca2c44091994724
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456289B2

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