Iodine → ethyl 6-chloro-8-(methylthio)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854937ノート

反応式

HRID 854937 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([S:12](Cl)(=O)=O)[CH:11]=1)[O:8][CH:7]([C:16]([F:19])([F:18])[F:17])[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:5]2.II.[C:27]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCN(CC)CC.CI>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([S:12][CH3:27])[CH:11]=1)[O:8][CH:7]([C:16]([F:19])([F:18])[F:17])[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:5]2

参加物

7

反応物 5

HCID 807IodineHCID 6328Methyl iodideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86599472ethyl 6-chloro-8-(chlorosulfonyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

生成物 1

HCID 69517271ethyl 6-chloro-8-(methylthio)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

To benzene (solvent) was added ethyl 6-chloro-8-(chlorosulfonyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate (Step 2, 0.68 g, 1.68 mmol), iodine (0.11 g, 0.84 mmol), and triphenyl phosphine (4.41 g, 16.8 mmol) amd the resulting mixture heated to reflux for 4 h and allowed to cool to RT and stand for 48 h. To this crude reaction was added Et3N (0.58 mL, 0.424 g, 4.20 mmol) and methyl iodide (0.06 mL, 0.13 g, 0.92 mmol). After extractive workup and silica chromatography the title compound was obtained as a yellow, crystalline mass (0.215 g, 36%). 1HNMR (CDCl3-d6/300 MHz) 7.59 (s, 1H), 7.07 (d, J=2.4 Hz, 1H), 6.98 (d, J=2.4 Hz, 1H), 5.78 (q, 1H, J=6.8 Hz), 4.20-4.40 (m, 3H), 2.42 (s, 3H), 1.33 (t, 3H, J=7.3 Hz).

後処理

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. customTo this crude reaction

出典と根拠

ORDレコード
ord-854dacd5a15945869312c701ece08c5d
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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