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

HRID 1992962ノート

反応式

HRID 1992962 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 204431481,4-Dioxane hydrochloride溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-821b33bd811f4374b4bef6037272625c
出典データセット
uspto-grants-2010_01
特許番号
US07649093B2

反応ノート

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