Tetrahydrofuran → HCID 13957671, compound

HRID 847452Notes

Reaction equation

HRID 847452 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[NH:4][C:5]([C:22](F)([F:24])[F:23])=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:7]([CH:14]([CH3:16])[CH3:15])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].C1CCN2C(=NCCC2)CC1.C1COCC1>O>[F:24][CH:22]([F:23])[C:5]1[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:7]([CH:14]([CH3:15])[CH3:16])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:3]([C:2]([F:27])([F:1])[F:26])[N:4]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13957629HCID 13957629, compound

Product 1

HCID 13957671HCID 13957671, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 50.0 g (0.124 mole) of diethyl 2,6-bis(trifluoromethyl)-1,4-dihydro-4-isopropyl-3,5-pyridinedicarboxylate, 18.87 g (0.124 mole) of DBU and 200 ml of THF is held at reflux for 18 hours and poured into water and extracted with ether. The ether extract is washed with diluted hydrochloric acid, dried (MgSO4) and concentrated. The residue is kugelrohr distilled at 1 torr to give 17.97 g (37.8%) of the desired product which is a liquid, nD25 1.4465.

Workup

  1. temperatureat reflux for 18 hours
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washis washed with diluted hydrochloric acid
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. distillationThe residue is kugelrohr distilled at 1 torr

Sources & evidence

ORD record
ord-47d9c0a2bb524ced846263009827d77a
Source dataset
uspto-grants-1992_08
Patent number
US05142055

Reaction notes

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