1,8-Diazabicyclo(5.4.0)undec-7-ene → 3,5-Diethyl 2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3,5-pyridinedicarboxylate

HRID 847453Notes

Reaction equation

HRID 847453 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[NH:4][C:5]([C:23](F)([F:25])[F:24])=[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:7]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].C1CCN2C(=NCCC2)CC1>C1COCC1>[F:25][CH:23]([F:24])[C:5]1[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:7]([CH2:14][CH:15]([CH3:16])[CH3:17])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:3]([C:2]([F:28])([F:1])[F:27])[N:4]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10916736HCID 10916736, compound

Product 1

HCID 108838203,5-Diethyl 2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3,5-pyridinedicarboxylateYield 50.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10.0 g (0.0240 mole) of diethyl 2,6-bis(trifluoromethyl)-1,4-dihydro-4-isobutyl-3,5-pyridinedicarboxylate, 3.65 g (0.0240 mole) of DBU and 150 ml of THF is held at reflux for 18 hours and concentrated. The residue is dissolved in ether and washed with diluted hydrochloric acid, dried (MgSO4) and concentrated. The residue is kugelrohr distilled at 0.1 torr to give 4.80 g (50%) of the desired product as an oil, nD25 1.4436.

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in ether
  4. washwashed with diluted hydrochloric acid
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. distillationThe residue is kugelrohr distilled at 0.1 torr

Sources & evidence

ORD record
ord-c92acfec9e5f4af4bdb58bb389fbcffa
Source dataset
uspto-grants-1992_08
Patent number
US05142055

Reaction notes

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