Tetrahydrofuran → HCID 13957671, compound

HRID 2308917Notes

Reaction equation

HRID 2308917 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-3422738ff229435fb712fa476df18030
Source dataset
uspto-grants-1987_09
Patent number
US04692184

Reaction notes

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