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

HRID 76261

반응식

HRID 76261 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 117685663-(Furan-2-yl)propanal수율 73%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5b81340e2f2a43a095bef81af588bf20
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835475B2

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