Benzene → HCID 68900235, compound

HRID 1435921Notes

Reaction equation

HRID 1435921 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([F:12])([F:11])[F:10])[C:4]=1NC(=O)OC(C)(C)C)=O.[C:21]([O:29][CH2:30][CH3:31])(=[O:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].N1[CH2:37][CH2:36][CH2:35]CC1.[C:38]([OH:46])(=[O:45])C1C=CC=CC=1.[CH:47]1C=CC=CC=1>O>[C:36]([O:46][C:38]([C:4]1[C:5]([C:9]([F:10])([F:11])[F:12])=[CH:6][CH:7]=[CH:8][C:3]=1[CH:1]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:21]([O:29][CH2:30][CH3:31])=[O:28])=[O:45])([CH3:35])([CH3:37])[CH3:47]

Participants

7

Reactant 5

HCID 241BenzeneHCID 243Benzoic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 53420013Tert-butyl 2-formyl-6-(trifluoromethyl)phenylcarbamate

Product 1

HCID 68900235HCID 68900235, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of tert-butyl 2-formyl-6-(trifluoromethyl)phenylcarbamate (0.40 g, 1.40 mmol) in 10 mL of benzene was added diethyl malonate (0.21 mL, 1.40 mmol), piperidine (0.015 mL, 0.15 mmol) and benzoic acid (17 mg, 0.14 mmol). The resulting mixture was allowed to stir at 80° C. for 6 h while water was collected in a Dean-Stark trap. The reaction was allowed to cool and was diluted with EtOAc. The organics were washed with 1N HCl, sat'd aq NaHCO3 and brine, dried (MgSO4), filtered through a pad of silica gel and concentrated in vacuo to afford 0.58 g (96%) of the title compound as an oil which solidified on standing. 1H NMR (CDCl3): δ 7.89 (s, 1H), 7.70-7.63 (m, 2H), 7.35 (t, 1H, J=7.7 Hz), 6.30 (broad s, 1H), 4.26-4.17 (m, 4H), 1.46 (s, 9H), 1.36-1.26 (m, 6H). LRMS (ESI): 432.32 (M+H)+.

Workup

  1. customwas collected in a Dean-Stark trap
  2. temperatureto cool
  3. additionwas diluted with EtOAc
  4. washThe organics were washed with 1N HCl
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered through a pad of silica gel
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f0ad3293c8b4d18930662cde8fdf842
Source dataset
uspto-grants-2009_11
Patent number
US07618980B2

Reaction notes

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