2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → ethyl (2E,4E,6E)-6-fluoro-7-(4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-methyl-octa-2,4,6-trienoate

HRID 2180518노트

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HRID 2180518 반응식
C(OP([CH2:9]/[C:10](/[CH3:17])=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.CN1CCCN(C)C1=O.C([Li])CCC.[F:32]/[C:33](=[C:36](/[C:38]1[CH:39]=[C:40]2[C:45](=[CH:46][C:47]=1[O:48][CH3:49])[O:44][C:43]([CH3:51])([CH3:50])[CH:42]=[C:41]2[CH:52]([CH3:54])[CH3:53])\[CH3:37])/[CH:34]=O>C1COCC1>[F:32]/[C:33](=[C:36](/[C:38]1[CH:39]=[C:40]2[C:45](=[CH:46][C:47]=1[O:48][CH3:49])[O:44][C:43]([CH3:51])([CH3:50])[CH:42]=[C:41]2[CH:52]([CH3:54])[CH3:53])\[CH3:37])/[CH:34]=[CH:9]/[C:10](/[CH3:17])=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13]

참가 물질

6

반응물 4

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 6000084Ethyl 4-(diethoxyphosphoryl)-3-methylbut-2-enoateHCID 22490793(2E)-2-Fluoro-3-(4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-but-2-enal2회HCID 178418339Butyllithium

생성물 1

HCID 86759708ethyl (2E,4E,6E)-6-fluoro-7-(4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-methyl-octa-2,4,6-trienoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a solution of ethyl 4-(diethoxyphosphoryl)-3-methyl-but-2E-enoate (240 mg, 0.91 mmol) in THF (10 mL), and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU, 0.13 mL) under argon at −78° C. was slowly added n-butyl lithium (1.6 M in hexanes, 0.60 mL, 0.96 mmol). The resulting mixture was stirred at −78° C. for 15 min before a solution of (2E)-2-fluoro-3-(4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-but-2-enal (Compound 95, 100 mg, 0.31 mmol) and THF (3 mL) was added via cannula. The resulting mixture was stirred at 0° C. for 1 h. The reaction was quenched with saturated NH4Cl, and the product was extracted with diethyl ether. The combined ethereal layers were washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 5% ethyl acetate in hexane) to yield the title compound as a yellow oil.

후처리

  1. customat −78° C.
  2. additionwas added via cannula
  3. customThe reaction was quenched with saturated NH4Cl
  4. extractionthe product was extracted with diethyl ether
  5. washThe combined ethereal layers were washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography (silica gel, 5% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-590a600b01244160bc2b885ed27a2294
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06887896B1

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