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

HRID 1481275
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HRID 1481275 반응식
[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]
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참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3a139e41ecd549b59d2b5428669133ef
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09409908B2

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