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Cornforth reagent → HCID 10195869, 화합물

HRID 1270212
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HRID 1270212 반응식
[C:1]([C:3]1[C:4]([O:16][CH3:17])=[CH:5][C:6]([O:14][CH3:15])=[C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)#[CH:2].C([Li])CCC.[CH3:23][O:24][C:25](=[O:40])[CH2:26][O:27][C:28]1[C:33]([O:34][CH3:35])=[CH:32][C:31]([CH:36]=[O:37])=[CH:30][C:29]=1[O:38][CH3:39].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C1COCC1>[CH3:23][O:24][C:25](=[O:40])[CH2:26][O:27][C:28]1[C:33]([O:34][CH3:35])=[CH:32][C:31]([C:36](=[O:37])[C:2]#[C:1][C:3]2[CH:8]=[C:7]([C:9]3[S:10][CH:11]=[CH:12][CH:13]=3)[C:6]([O:14][CH3:15])=[CH:5][C:4]=2[O:16][CH3:17])=[CH:30][C:29]=1[O:38][CH3:39]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 2724130Cornforth reagentHCID 18449299HCID 18449299, 화합물HCID 43516604HCID 43516604, 화합물HCID 178418339Butyllithium

생성물 1

HCID 10195869HCID 10195869, 화합물수율 49.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매
2회

실험 절차

Ex-3: A solution of 2-(5-ethynyl-2,4-dimethoxy-phenyl)-thiophene (1.0 g, 4.09 mmol) from Ex-1B in THF (35 mL) was cooled to −78° C. n-Butyllithium (4.62 mmol, 1.85 mL of a 2.5 M solution in hexanes) was added over 15 min while maintaining an internal temperature below −50° C. After aging for 15 min at −78° C., the reaction was transferred via cannula over 5 min to a cold (−78° C.) solution of (4-formyl-2,6-dimethoxy-phenoxy)-acetic acid methyl ester (1.15 g, 4.52 mmol) from Ex-3A in THF (25 mL). The resulting solution was slowly warmed to room temperature and then quenched with a saturated NH4Cl solution. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic phases were dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure The resulting crude {4-[3-(2,4-dimethoxy-5-thiophen-2-yl-phenyl)-1-hydroxy-prop-2-ynyl]-2,6-dimethoxy-phenoxy}-acetic acid methyl ester was dissolved in dichloromethane (50 mL), charged with pyridinium dichromate (3.00 g, 7.97 mmol) and aged at room temperature under nitrogen for 2.5 h. The reaction was then filtered through a pad of celite using additional dichloromethane and then ethyl acetate. The combined organic was concentrated under reduced pressure. Silica gel chromatography (ethyl acetate/hexane, 3:2) gave 1.0 g (49%) of the desired {4-[3-(2,4-dimethoxy-5-thiophen-2-yl-phenyl)-propynoyl]-2,6-dimethoxy-phenoxy}-acetic acid methyl ester as a yellow solid, m.p. 153–155° C. 1H-NMR (300 MHz, CDCl3) δ 7.89 (s, 1H), 7.60 (s, 2H), 7.41 (dd, 1H, J=3.6 and 1.5 Hz), 7.35 (dd, 1H, J=5.3 and 1.5 Hz), 7.09 (dd, 1H, J=5.3 and 3.6 Hz), 6.54 (s, 1H), 4.77 (s, 2H), 4.01 (s, 3H), 3.99 (s, 3H), 3.97 (s, 6H), 3.82 (s, 3H).

후처리

  1. additionwas added over 15 min
  2. temperaturewhile maintaining an internal temperature below −50° C
  3. customquenched with a saturated NH4Cl solution
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organic phases were dried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure The resulting crude {4-[3-(2,4-dimethoxy-5-thiophen-2-yl-phenyl)-1-hydroxy-prop-2-ynyl]-2,6-dimethoxy-phenoxy}-acetic acid methyl ester
  8. dissolutionwas dissolved in dichloromethane (50 mL)
  9. waitaged at room temperature under nitrogen for 2.5 h
  10. filtrationThe reaction was then filtered through a pad of celite
  11. concentrationThe combined organic was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d687e27392644fd7af5f936828ee1c68
출처 데이터셋
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07202247B2

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