Dimethylformamide → ethyl 8-iodo-7-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 855023ノート

反応式

HRID 855023 の反応式
[OH:1][C:2]1[C:9]([I:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[F:13][C:14](/[C:17](=C\C)/C(OCC)=O)([F:16])[F:15].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O.[C:36]([O:39][CH2:40][CH3:41])(=[O:38])[CH3:37]>>[I:10][C:9]1[C:8]([O:11][CH3:12])=[CH:7][CH:6]=[C:3]2[C:2]=1[O:1][CH:17]([C:14]([F:16])([F:15])[F:13])[C:37]([C:36]([O:39][CH2:40][CH3:41])=[O:38])=[CH:4]2

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 190890572-Hydroxy-3-iodo-4-methoxybenzaldehydeHCID 23051828Ethyl trifluoromethylcrotonate

生成物 1

HCID 58934894ethyl 8-iodo-7-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate収率 14%

反応条件

温度
90 °C

実験手順

To the mixture of 1.5 g (5.4 mmol) of 2-hydroxy-3-iodo-4-methoxybenzaldehyde, 3.1 mL (20.6 mmol) of ethyl trifluoromethylcrotonate, and 4.2 g(12.9 mmol) of cesium carbonate was added 8 mL of anhydrous N,N-dimethylformamide. The mixture was heated to 90° C. overnight. After cooling to room temperature, to the reaction was added 150 mL of ethyl acetate. The organic solution was filtered, washed with brine and dried over anhydrous magnesium sulfate. After removing the volatiles, the residue was purified by silica chromatography with ethyl acetate/hexane (2:8) to give 0.3 g (14%) a light yellow solid: 1H NMR(CDCl3/400 MHz) 7.65(s, 1H), 7.17(d, J=8.4 Hz, 1H), 6.50(d, J=8.4 Hz, 1H), 5.80(q, J=6.8 Hz,1H), 4.30(m, 2H), 3.92(s, 3H), 1.33(t, J=7.6 Hz, 3H). MS (ESI+) 429.0(M+1, 100). HRMS (EI+) m/z calcd for (C14H12F3O4) 427.9732, found 427.9715.

後処理

  1. temperatureAfter cooling to room temperature, to the reaction
  2. filtrationThe organic solution was filtered
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removing the volatiles
  6. customthe residue was purified by silica chromatography with ethyl acetate/hexane (2:8)

出典と根拠

ORDレコード
ord-85b4db35c8b64128bac6b94fbe2ef3c4
出典データセット
uspto-grants-2007_08
特許番号
US07259266B2

反応ノート

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