Triacetoxyperiodinane → 3-(Furan-2-yl)propanal

HRID 76261

反応式

HRID 76261 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][OH:9].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH:8]=[O:9]

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 2271783-(Furan-2-yl)propan-1-ol

生成物 1

HCID 117685663-(Furan-2-yl)propanal収率 73%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The product from Example 50A (2.0 g, 15.9 mmol) in CH2Cl2 (50 mL) was treated with Dess-Martin periodinane (8.1 g, 19.2 mmol) in portions. The mixture was stirred at rt for 2 hrs, quenched with saturated NaS2O3, and the mixture was extracted with CH2Cl2. The CH2Cl2 layer was washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated. The resulting residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 1.44 g (73%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 2.80 (t, J=8.24, 6.41 Hz, 2 H) 2.98 (t, J=7.32 Hz, 2 H) 6.02 (d, J=3.97 Hz, 1 H) 6.19-6.36 (m, 1 H) 7.28-7.33 (m, 1 H) 9.82 (s, 1 H).

後処理

  1. customquenched with saturated NaS2O3
  2. extractionthe mixture was extracted with CH2Cl2
  3. washThe CH2Cl2 layer was washed with saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography

出典と根拠

ORDレコード
ord-5b81340e2f2a43a095bef81af588bf20
出典データセット
uspto-grants-2014_09
特許番号
US08835475B2

関連ノート

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