Furan → HCID 12194348, 화합물

HRID 1504392노트

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HRID 1504392 반응식
O1C=CC=C1.[C:6]([O:10][CH2:11][CH3:12])(=O)[CH:7]=[CH2:8].[C:13]([O:16][CH2:17][CH3:18])(=[O:15])[CH3:14]>[I-].[Zn+2].[I-]>[C@@H:6]12[O:10][C@@H:11]([CH:8]=[CH:7]1)[CH2:12][C@H:14]2[C:13]([O:16][CH2:17][CH3:18])=[O:15]

참가 물질

5

반응물 3

HCID 8029FuranHCID 8821Ethyl AcrylateHCID 8857Ethyl Acetate

생성물 1

HCID 12194348HCID 12194348, 화합물수율 46.5%

시약·촉매·용매 1

HCID 9883512zinc(II)iodide촉매

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온도
40 °C

실험 절차

A flask was charged with zinc iodide (1.010 ml, 14.98 mmol), then heated with a heat gun under high vacuum for 5 minutes. The flask was charged with furan (5.09 ml, 69.9 mmol) and ethyl acrylate (5.43 ml, 49.9 mmol), then covered in foil and heated at 40° C. for 48 hours. The solution was then diluted with ethyl acetate and washed with 10% aqueous Na2SO3. After drying with Na2SO4 and filtration, the solvents were removed under reduced pressure then purified by silica gel chromatography (RediSep Gold 80 g, gradient elution 0-50% EtOAc:Heptane) to afford (1R,2R,4R)-ethyl 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate (3.91 g, 23.25 mmol, 46.5% yield) as a clear colorless oil (2.5:1 mixture of endo and exo isomers). 1H NMR (400 MHz, CHLOROFORM-d) δ=6.44 (dd, J=1.7, 5.8 Hz, 1H), 6.41-6.38 (m, 1H), 6.38-6.34 (m, 1H), 6.24 (dd, J=1.6, 5.8 Hz, 1H), 5.19 (dd, J=0.7, 1.6 Hz, 1H), 5.18-5.16 (m, 1H), 5.08 (dd, J=0.7, 4.6 Hz, 1H), 5.02 (ddd, J=0.7, 1.7, 4.7 Hz, 1H), 4.19 (q, J=7.1 Hz, 2H), 4.10 (ttd, J=3.6, 7.1, 10.7 Hz, 1H), 3.11 (ddd, J=3.8, 4.9, 9.1 Hz, 1H), 2.42 (dd, J=3.9, 8.5 Hz, 1H), 2.17 (td, J=4.4, 11.2 Hz, 1H), 2.11 (ddd, J=4.7, 9.3, 11.4 Hz, 1H), 1.60 (dd, J=3.8, 11.5 Hz, 1H), 1.56 (dd, J=8.6, 11.6 Hz, 1H), 1.29 (t, J=7.2 Hz, 3H), 1.25 (t, J=7.2 Hz, 1H)

후처리

  1. temperatureheated with a heat gun under high vacuum for 5 minutes
  2. washwashed with 10% aqueous Na2SO3
  3. dry with materialAfter drying with Na2SO4 and filtration
  4. customthe solvents were removed under reduced pressure
  5. customthen purified by silica gel chromatography (RediSep Gold 80 g, gradient elution 0-50% EtOAc:Heptane)
  6. customto afford

출처 및 근거

ORD 기록
ord-80f1714f900948be80f620b7c1505328
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212182B2

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