3,4,5-Trimethoxybenzaldehyde → HCID 16110327、化合物

HRID 273343

反応式

HRID 273343 の反応式
[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]

参加物

4

反応物 2

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 178463197HCID 178463197、化合物

生成物 1

HCID 16110327HCID 16110327、化合物収率 73.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-706fa45e5dde4051bca2c44091994724
出典データセット
uspto-grants-2008_11
特許番号
US07456289B2

関連ノート

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