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Trifluoroacetic acid → Methyl (4-formyl-3-nitrophenyl)carbamate

HRID 1481275
ノート
印刷プレビュー

反応式

HRID 1481275 の反応式
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:16])[O:14][CH3:15])=[CH:8][C:7]=1[N+:17]([O-:19])=[O:18].C(O)(C(F)(F)F)=O>O>[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:16])[O:14][CH3:15])=[CH:8][C:7]=1[N+:17]([O-:19])=[O:18])=[O:1]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 71263042Methyl (4-(1,3-dioxolan-2-yl)-3-nitrophenyl)carbamate

生成物 1

HCID 89410473Methyl (4-formyl-3-nitrophenyl)carbamate収率 92%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

5C (5.00 g, 18.64 mmol) was added to a solution of TFA (27 mL) and H2O (3 mL) and stirred at rt for 3 h. After 3 h, the reaction mixture was concentrated and the residue was partitioned between H2O and EtOAc. The organic layer was then washed with saturated sodium bicarbonate solution followed by brine. The organic layer was then dried over sodium sulfate, filtered, and concentrated to give a light yellow solid as 5D (3.83 g, 92%). 1H NMR (400 MHz, DMSO-d6) δ 10.59 (s, 1H), 10.09 (s, 1H), 8.23 (d, J=1.6 Hz, 1H), 7.92 (d, J=8.2 Hz, 1H), 7.86-7.81 (m, 1H), 3.74 (s, 3H) ppm.

後処理

  1. waitAfter 3 h
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was partitioned between H2O and EtOAc
  4. washThe organic layer was then washed with saturated sodium bicarbonate solution
  5. dry with materialThe organic layer was then dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-3a139e41ecd549b59d2b5428669133ef
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409908B2

反応ノート

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