Potassium Carbonate → ethyl 6-nitro-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylate

HRID 722292

反応式

HRID 722292 の反応式
[N+:1]([C:4]1[CH:11]=[C:8]([CH:9]=O)[C:7]([OH:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:13][C:14]([F:23])([F:22])/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.C(OCC)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH:15]([C:14]([F:13])([F:23])[F:22])[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:9][C:8]=2[CH:11]=1)([O-:3])=[O:2]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 668085-NitrosalicylaldehydeHCID 5371261Ethyl (2E)-4,4,4-trifluoro-2-butenoate

生成物 1

HCID 21883718ethyl 6-nitro-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A mixture of 5-nitrosalicylaldehyde (4.80 g, 28.7 mmol) and ethyl 4,4,4-trifluorocrotonate (6.6 g, 39.4 mol) in anhydrous DMF was warmed to 60° C. and treated with anhydrous K2CO3 (3.90 g, 28.9 mol). The solution was maintained at 60° C. for 20 hours, cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic extracts were washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacua to afford an oil. The oil was dissolved in diethyl ether (5 mL). Hexanes was added until the solution became cloudy. Upon standing at room temperature overnight the ester was obtained as yellow crystals (0.856 g, 7% yield). This material was of sufficient purity to be used in subsequent steps without further purification. 1H NMR (CDCl3/300 MHz) 8.15–8.19 (m, 2H), 7.74 (s, 1H), 7.09 (d, 1H, J=8.9 Hz), 5.81 (q, 1H, J=5.8 Hz), 4.29–4.39 (m, 2H), 1.35 (t, 3H, J=6.0 Hz),

後処理

  1. temperatureThe solution was maintained at 60° C. for 20 hours
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacua
  8. customto afford an oil

出典と根拠

ORDレコード
ord-684e61751e574bbc8516c34e94ddaa94
出典データセット
uspto-grants-2006_11
特許番号
US07138411B2

関連ノート

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