Cesium carbonate → 4-(6-Methoxy-3-methyl-2-thiophen-3-yl-naphthalen-1-yloxy)-benzaldehyde

HRID 1992962노트

반응식

HRID 1992962 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][CH2:14]OC)=[C:8]([C:17]1[CH:21]=[CH:20][S:19][CH:18]=1)[C:7]([CH3:22])=[CH:6]2.C([O-])([O-])=O.[Cs+].[Cs+].FC1[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=1>Cl.O1CCOCC1.O.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=1)=[C:8]([C:17]1[CH:21]=[CH:20][S:19][CH:18]=1)[C:7]([CH3:22])=[CH:6]2

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 685377683-(6-Methoxy-1-(methoxymethoxy)-3-methyl-naphthalen-2-yl)-thiophene

생성물 1

HCID 860871844-(6-Methoxy-3-methyl-2-thiophen-3-yl-naphthalen-1-yloxy)-benzaldehyde수율 74%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 204431481,4-Dioxane hydrochloride용매

실험 절차

A solution of 3-(6-Methoxy-1-methoxymethoxy-3-methyl-naphthalen-2-yl)-thiophene (199) (0.347 g, 1.10 mmol) in 4 N HCl/Dioxane (5 mL) was stirred at room temperature for 30 min. The solvent was removed from the reaction mixture, then dissolved in DMSO (3 mL) followed by addition of Cs2CO3 (0.899 g, 2.76 mmol) and 4-fluorobenzaldehye (0.142 mL, 1.32 mmol). The reaction mixture was irradiated with microwave at 80° C. for 4.5 h. Reaction mixture was diluted with water and EtOAc, separated the layers, then the aqueous layer was extracted with EtOAc. The combined organic layer was washed with water followed by brine, dried over Na2SO4, filtered and concentrated. The crude material was purified with a gradient of 5% EtOAc in hexanes over 50 min to afford 0.304 g (74%) of the title compound (200) as oil. 1H NMR (400 MHz, d-CDCl3): δ 2.32 (s, 3H), 3.93 (s, 3H), 6.74 (d, J=8.6 Hz, 2H), 6.90-6.91 (m, 1H), 7.02-7.06 (m, 2H), 7.13 (m, 1H), 7.20-7.22 (m, 1H), 7.58 (s, 1H), 7.65 (d, J=8.7 Hz, 2H), 7.69 (d, J=9.2 Hz, 1H), 9.81 (s, 1H).

후처리

  1. customThe solvent was removed from the reaction mixture
  2. dissolutiondissolved in DMSO (3 mL)
  3. customThe reaction mixture was irradiated with microwave at 80° C. for 4.5 h
  4. customReaction mixture
  5. customseparated the layers
  6. extractionthe aqueous layer was extracted with EtOAc
  7. washThe combined organic layer was washed with water
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude material was purified with a gradient of 5% EtOAc in hexanes over 50 min

출처 및 근거

ORD 기록
ord-821b33bd811f4374b4bef6037272625c
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07649093B2

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